J buckingham, r a hill (auth ) atlas of stereochemistry absolute configurations of organic molecules springer US (1986)
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Atlas of
Stereochemistry
SUPPLEMENT
ATLAS OF
STEREOCHEMISTRY
Absolute Configurations o/Organic Moleeules
Second Edition
SUPPLEMENT
J. Buckingham
Chapman and Hall, London
and
R.A. Hill
University
0/ Glasgow
Springer-Science+Business Media, B.Y.
ISBN 978-0-412-26000-1
ISBN 978-1-4899-3420-8 (eBook)
DOI 10.1007/978-1-4899-3420-8
© 1986 J. Buckingham and R.A. Hili
Originally published by Chapman and Hall in 1986.
Softcover reprint ofthe hardcover 2nd edition 1986
All rights reserved. No part of this book may be reprinted,
or reproduced or utilized in any form or by any electronic,
mechanical or other means, now known or hereafter
invented, inc1uding photocopying and recording, or in any
information storage and retrieval system, without
permission in writing from the publisher.
British Library Cataloguing in Publication Data
Klyne, William
Atlas of stereochemistry: absolute configurations of
organie molecules.-2nd ed. supplement
1. Stereochemistry-Atlases
I. Title, 11. Buckingham, J. 111. Hill, R.A. 547.1'223
00481
Library of Congress Cataloging in Publication Data
Buckingham, J.
Atlas of stereochemistry, absolute configurations of
organic molecules, second edition. Supplement.
Supplement to: Atlas of stereochemistry: absolute
configurations of organie molecularesIW. Klyne and J.
Buckingham. 2nd ed. London, 1978.
Bibliography: p.
Inc1udes indexes.
1. Stereochemistry-Atlases. I. Hill, R.A., 195111. Klyne, William. Atlas of stereochemistry.
111. Title.
00481.K64 1978 Suppl. 541.2'23 85-12825
Contents
PREFACE TO THE SUPPLEMENT
KEY TO THE SUPPLEMENT
A"
Fundamental Chiral Compounds
C'
Carbohydrates
T'
Terpenes (including Steroids)
K"
Alkaloids
Y"
Miseellaneous Natural Produets
D"
Compounds with Chirality due to Isotopie Substitution
X"
Compounds exhibiting Axial or Plan ar Chirality;
gyroehiral mole eule , ete.
Z"
Compounds eontaining Chiral Atoms other than Carbon
CUMULATIVE FORMULA INDEX
CUMULATIVE AUTHOR INDEX
CUMULATIVE SUBJECT INDEX
Vll
Vlll
1
53
57
103
115
139
147
161
173
267
297
Preface to the Supplement
Tbe determination of absolute configurations is now a central and routine part of research in
organic chemistry and biochemistry. Since the publication of the second edition of the Atlas in
1978, many hundred further important determinations have been carried out, more than
justifying the present publication of an extensive supplement.
Despite some expectations to the contrary, direct Bijvoet X-ray determinations have not
completely dominated the field in the last seven years. Chemical correlations continue to be the
method of choice for most types of compound except complex natural products; the correlation
charts which are the raison d' etre of this publication continue to prosper , as perusal of the pages
of this supplement will show.
Once again, our thanks to those reviewers and correspondents who have sent in their
comments on published correlations. Tbere have been relatively few absolute configuration
reversals during the last seven years, leading to the presumption that the vast majority of the
determinations so far recorded in the Atlas will stand the test of time.
J. Buckingham
R.A. Hill
Key to the Supplement
Scope
The coverage of the Supplement corresponds with that of the Second Edition main volumes,
except that organometallic compounds have been omitted.
Literature coverage
The literature has been scanned to the end of 1982, and a few important references from 1983 have
been included. There are also a considerable number of pre-1976 correlations included for the first
time.
Numbering of formulae and cross-references
The arrangement of chapters is the same as in the Main Work. In the supplement each compound
reference carries a second prime. Thus A32.2 refers to volume 1 of the Main Work, A'32.2 to
volume 2, and A"32.2 to the Supplement.
Important generalliterature references
Proposals modifying the Cahn-Ingold-Prelog system of configurational notation have been put
forward by V. Prelog and G. Heimchen (Angew. Chem., Int. Ed. Eng/., 1982, 21, 567).
1977 saw the publication of the major work Stereochemistry Fundamentals and Methods, Georg
Thieme Verlag. In particular volume 3 is entitled 'Determination of ~onfigurations by Chemical
Methods' and volume 4, by J. Jaques, C. Cross and S. Bourcier gives the absolute configurations
of 6000 selected compounds with one chiral carbon atom in tabular form.
For a discussion of the Bijvoet X-ray anomalous dispersion method, see D. Rogers, Acta
Crystallogr. Sect. B., 1979, 35, 2823.
The publication of the series Atlas of Three-dimensional structure of drugs (Janssen Research
Foundation Series) began in 1979 with Vol. 1 edited by J.P. Tolleaere,'H. Moereels and L.A.
Raymaekers, published by Elsevier, Amsterdam.
The theory of 'hyperchirality' advanced by J. Dugundy, D. Marquarding and I. Ugi (Chem. Ser.
1976,9, 74; 1977, 11, 17), seems to have passed into the limbo of history (W. Hasselbarth, ibid,
1976, 10, 96; 1977, 11, 148; C.A. Mead, ibid, 1976, 10, 101; 1977, 11, 145).
A"
Fundamental
Chiral Compounds
Sub-c1assification of compounds in chapter A"
Class
Pages
la
Al"
Ib
All"
2a
2b
3a
3b
4a
4b
A21"_A44", A47"
A2S , A4O"_A46"
A 2"_A I6", A 2 1"
A ll"_A20"
A 47"_Aso"
A 49"_Aso"
1
Class 1a
(SK-) I-omillo- 2- methylproponephosphO"ic acid.
Abs. X"OY [I]
1. T. Glowiak, W. Sawka-Dobrowalska, J. Kowalik, P. Mastalerz, M. Soroka and J. Zon, Tetrahedron Lett.,
3
1m, 3965.
A 2"
Class 2a
[0)
'l7J
I. ($ l- (+) 2· thlO
U
2 .( 111, 2S)-(+)2d>lo,ocyclohuanol .
hoxa>otlO. By OAO l7J.
':i:
~Ct
I
i 5 .(I1H·l2-.,..lolYoyolo·
i
,
ho.onono. By 0100 (7].
. ... _._.. .. ._.. ._.. ._.. .. ._ ._._._ ._ ... _.. .__ .. ._._.1._._._._._._ .. ._ .. .. ._ .
H+\
CH]
(211,311)-(+l2,3dib'omobuton. A,'.IS.
_ ._ ._ . _._ ._ .__ . - '--- -- ''' 1
C2H~
(I1H-) 2-brcmobulone
A1.1I .
·,,1[6)
a,-f
CH 2
~C~I
B'+H.
CH]
C(2)
-W-
H
CB'2 0i 3
4.(R)-(+l(2-iodoothyll·
oxirane.
!
7. (R H+) 2,2,3-lribromo -
L._.. .__ . .. .~ul~n~
• _ • . __
NH
H+COOH
CH,cHzOH
S·(-)dihydrocou .... rille oeid
8. ($). (-) 5-mell>olY·
dihydroeoumorilic ocid.
YI.12.
(SH ) 2-omlno- 4hyd,oxybulonoe ocie!
(SH-lmolio ocid
AI.2'·
10. (I1H 1 5u-23397.
A" . 7.
11. (S,SH lavonoe acie! 8.
12. (5) · (-) I, 4- dibromo-
11. (~ S H+)eycloh ..yl·18 crown-6 ,
butan~ 2 -ol.
L
15. (5H-) (2- b,omoethylloxirane Y" 10.
._ . _ ._ ._ ._ ._ ._ . _ ._ . _ ._ . _ . ...
C
-c;r14. (~S,S,5H+ldieyel ohoxyl·
18-crown·6 .
1.
2.
3.
4.
5.
6.
7.
8.
9.
(IS, 25l· (+leyeloh ..on.·
I,Z-diol A 16.13.
1'. (5,5,5,5)-(+) bi.(2hydr.lycyciohnyll
18. (5,sH+lcyclohoxyl1:;-c,.wn· 5 .
ether,
G. Lowe and B.V.L. Potter, J. Chern. Soc., Perkin Trans. 1, 1980, 2029.
S. Fushiya, Y. Sato and S. Nozoe, Chern. Lett. 1980, 1215.
B. Seuring and D. Seebach, Helv. Chirn. Acta, 1977, 60, 1175.
N.K. Chauduri, T.l. Ball and N. Finch, Experientia, 1977, 33, 575.
D.L. Boger and l.S. Panek, J. Org. Chern., 1981, 46, 1208.
D.D. Tanner, G.V. Blackburn, Y. Kosugi and T.C.S. Rao, J. Arn. Chern. Soc., 1977, 99, 2714.
R.L. Coumbie, D.D. Ridley and G.W. Simpson, Chern. Cornrn., 1977, 315.
R.C. Hayward, C.H. Overton and G.H. Whitham, J. Chern. Soc., Perkin Trans. 1, 1976, 2413.
P.G. Barili, G. BeUucci, G. Ingrosso and A. Vatteroni, Gazz. Chirn. Ila1., 1977, 107, 147.
4
i <S)-(-lpn>pylo.irono
A15.18 .
A
3
Class 2a
CHO
~ (l.i,-:-_c.[~,;I_)-- Hr~: CH~_M_'_2_C. ,.[~-=;)
. :;;-,f':O
__
~
~
( )O- Iuc",.
(6- deoxy- o-9Olocto •• )
~
) 2 - deoxy-
I. (R)-(- )6-melhy lhept-5-en-Z-ol
(.ulcotol).
1418 .1 7'.
111
D-,ibo•• C1.8 .
C~l
CH 2CHz°H
H+OH
CH,
(R)-(-)hoptodocon3-01 147'. 3 .
tttrodtc·4E"'enoic
""id. MI ether (-I .
."ore-).
("I)
C 2
•
CCH )..rH
H,
~
[$)
CH=CHCCHz1sCH.
1.9Z-diln-4.6-diyn3.8-diol (Iolee,indiol).
OH
diethylsuccinic acid
1445.5.
CCHz)6CH 3
CCHz)6CH•
(CH2'~CH3
8. (RH-13 -hydroxydoconoic
8-01.
. ----....
(01.
[4)
H+OH
5 . (RH )heptodecon-
acid . Me fltlur (-) .
(R)-(- ) 3-hydroxy
non a noic ocid
14 7'.8.
c:x: a
COOH
H;=F~H
Q~
[6)
C(1)
~
7.
"COOH
(lR,ZR)-(-)
cyclohexone· , , 2 -
(2S.~H+)2.3-
dimercopto5UCcinic
acid . di- Me ether (+)
S,S-di-MoC+).
COOH
OR
~[6
J
COOH
COOH
(ZR.3RH+IZ.3-
m.fhyloxetan• .
.---- .... Hr:HOH
CH 2COOH
2""'3
H+
4 . (3R.8S)-(-lhoptedece-
H~~=F~2H~
CH.
3. (RH- 1Z -
[al. j (4)
HO+H
COOH
H+b
CH 2CH 2
t
cG;=CH 2
H~OH
W-
(Rl- C-Ibutone'.3-dlol
AI. 12 .
(RH ) 3-hydroxybutenoic
acid A8.4 .
Mo "'hor(-)'
EI
2 .(RH-13-hydroxy-
C(2)
dicorbox)llic. ocid
8 . CZS,3SI-f-) 1.4-d,tNone-
1437'.
e.
2,!-dlCgrboxyhc aCid.
1.
2.
3.
4.
5.
6.
K. Mori, Tetrahedron, 1981, 37, 1341.
H.R. Schuler and K.N. Slessor, Can. J. Chern., 1977, 55, 3280.
M. Segi, T. Takebe, S. Masuda, T. Nakajima and S. Suga, Bull. Chern. Soc. Jpn., 1982, 55, 167.
J.H. Cardellina, D. Dalietos, F.-J. Marner, J.S. Mynderse and R.E. Moore, Phytochernistry, 1978, 17, 2091.
E. Lemmich, Phytochernistry, 1981, 20, 1419.
M.O. Hedblom, Ark. Kerni, 1969, 31, 489.
5
1!
A
4"
Class 2a
-
CH 3
[0]
[HJ
-----.
HO+H
[<'J
CH zCH zCOCH 3
[2]
2. (R)-(-)5'nydroxy-
CH 3
- +J
Ni/Ha
HO+H
(%~CH3
A·5.0 .
(%)4 CH 3
(% )3CH 3
H+OH
H+OH
CH-CH 2
... (SH-)2-hydroxy'
heptanoic Qckt
lJ. (S)-(+)O
""planol.
A· ... S.
(C~ )3CH2
S
AOd phlholote (-l.
By chiro l nmr [2],
(S )-(+l2-hydroxy-
O .· OH
==
5. (SH-)thiopon-3·0I .
(R)' '''',on'2-01
huon-2-ontl .
2S
CH H
HO
(tJ
.li(-,J
H+)~H3
~C=CH
~~CH3
S. (SH-loc\·l-yn-4-01.
By AS(H)
[.J].
1. (S)-001""·4 -01.
No detoelobl. rolalion .
bonzool. (-I, phlholol. (-I.
+
(al. 1[JJ
+
CH2~CH3
H+):3
H+OH
C=CH
CH2CH3
(RH-)oc\on·3··01
C=CH
(S)-(- )0<1+ yn-3-0I
(S)-( - )""'+yn-
__
3-01 A 8.1l1.
Y'·.I1.
_._._._._._._._._._._._._._._._._._._._._._._. __ ._._.-.-.-._._._._._.-._._.
__Y·S.18.
._._._._._._.,._._._._.
._._._._._._.-
C~COOH
~:~.
H+OH
CH2CHzCH 3
C~CH,pH
~
H+OH
~~CH3
10. (RH-)hoxono-',3-diol.
(R)-(-l3-hydroxy'
huanoic aeid
!+H- 0
CH zCH 2
:CH~CH3 :
i
CHzCHzCH 3
11. (S)-(-l2·propyIlWetane.
(RH+) 3-hydroty- 4
m.lhylpontc>noie acid
AS.2 .
A 8.15.
_._._._.- ._. - ._. _. _._._.- . _._. __ . _. __ ._._.- ' - ' - ' - ' T ' - ' - ' - ' - ' _ . _ . - ._._. __ ._. _._. __ ._._. __ ._.-t
+
C(41
COOH
C""CCH 3
H
OH
CH 2 CH(CH s)2
12. (RH+)6- molhylhopt2-yn-4-01.
8y AS(Hl (8].
1.
2.
3.
4.
5.
6.
7.
8.
9.
CHzPl1
<:(21
~
H+OH
H+OH
CH:2CH(CH S )Z
CH(CH 5 )z
(R H +) 2- hydroxy- 4molhyl~nlanoie
A· ... 2.
t C7]
14. (SH-)3-molhyl-4-
oeid
phonylbulan- 2-01.
J.B. Jones and H.M. Schwartz, Can. J. Chern., 1981, 59, 1574.
B.R. Davis, G.W. Rewcastle, R.J. Stevenson and P.D. Woodgate, J. Chern. Soc., Perkin Trans. 1, 1977, 2148.
W.J. McGahren, K.J. Sax, M.P. Kunstmann and G.A. Ellestad, J. Org. Chern., 1977, 42, 1659.
D.W. Connell and M.D. Sutherland, Aust. J. Chern., 1969, 22, 1033.
P.A. Levene and A. Walti, J. Biol. Chern., 1931, 94, 593.
D.R. Crump, Aust. J. Chern., 1982, 35, 1945.
J.P. Vigneron, M. Dhaenens and A. Horeau, Tetrahedron, 1977, 33, 507.
K. Chan, N. Cohen. J.P. DeNoble, A.C. Specian and G. Sauey, J. Org. Chern., 1976, 41, 3497.
W.J. Elliott and J. Fried, J. Org. Chern., 1976, 41, 2469.
6
A 5"
Class 2a
Cl"
s]
COOH
~N+H
Sr
H
"'=t-
COOH
CXXlH
C(2)
~
CH 3
H
OH
CU)
sr+H
H
OH
~
(2S ,3RH-)2-omino
3-bromol>uty.-ic ocid.
3-hydroxybul)'rie ocid
• e. 18.
-.:ro--+
~J]
013
3
1. (2R ,3SH+)2-omino-
COOH
C(21
~-rHOIH
OH
H=F H
~N
01 3
2 . (2S,3RH )-2-bromo-3hydroxybutyric aold .
01 3
5 . (2R ,3S H+)3'omino2 - hydroxybutyric ocid
(l101"'eonine)_
(25,3$H+)2-omino3- hydroxybul)'r ic oeld
A24 . 2.
---- -- -- -- -- -- ------- - -- -- -- -- --- ------ ------- -- ------ ------------ -- -- -- ------- - -- ---- -- -- -- -- ------- --- -- --- - -- ------------ -l
00':~0 """"0""'r \ C2H~
C)-CHO
s
4. (S H + >tot'ohydrothiophono-2c:orboxoldolydo _
0=-C>-(CH2)4013
0
""'0···'0Y.'7
5. (2R,5SH+)2'
Ithyl-1 J6-diow:o-
6. (RH+)4-hydroxyhoxonoic
I
oc;id loctcn • .
acid lacton • .
spiro (4_4J nonono _
Hj[6J
C(21/
/[.!J]
o-COOH
s
11. (S H+ltotrohydro '
lhiop/Itne · 2 -
7. (R)-(+)4,-hycl roxynononoic
:
,
CH3
:
i
O~OH
lotrohydrothiophone.
carbo:rylic acid
(5) -( +) 4, 5-dihydroxyp,n1anotc ocid 1J 4- lactor.
AI1 .1 2 .
• '8.2_
8 125,35)( )2·amino3- mercoptobJt)'ric acid
iL . _
o
10. (R)-{-)2-hydroxymolhyl'
~,
. _ . _ . _._ . _ . _ . _. _ . _
(5 H+) t-arninoinclono
"ydrocrllotlde H
A25.17.
C(3Ij[4]
C(2)![6]
C)-CH==CHCH 3
s
11. (5)2-(2-proponyl)-
totrohydrothiophono _ j
90th _
_ ;so",." (4).
12. (5H+) butono-
(5)-(+) IIlutamic
acid A 11_7.
1,,3-diamin• .
C(~I![/]
15. (5)-(+)3-ominop'opooo'
l,I,3'1'icGtboxylic
(J -ca,boxYlilulomic) acid_
14. (SH )3-"""""'dipic
ocid _
N-benzyloxycorbonyl,
15. (S)-(+)2'amlno-2-
(5-t.l,az~yl) butyrie acid_
(5H+)2-aminoadipic
~ r:~'d
A 25.11.
(5)-(+) 2,5-diomino'
pontonoic acid .11. 15.
[0) ~
18. (5)-(+)4-omlnohox5- ynoic acid.
17. (5H )2,6diam,nohox'l-yne_
hvd,ochlorldo (+).
The correlation All.15-+A18.2 is said to be dubious [6].
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
T.T. Van, E. Kojro and Z. Grzonka, Tetrahedron , 1977, 33, 2299.
P. Casara, C. Danzin, B.W. Metcalf and M.J. Jung, Chern. Cornrn., 1982, 1190.
J.L. Morell, P. Fleckenstein and E. Gron, J. Org. Chern., 1977, 42, 355.
See p. All.
U. Ravid, R.M. Silverstein and L.R. Smith, Tetrahedron , 1978, 34, 1449.
G. Stork and A.F. Kreft, J. Arn. Chern. Soc., 1977, 99, 3851.
L.R. Smith, H.J. Williams and R.M. Silverstein, Tetrahedron Lett., 1978, 3231.
E. Balieu, P.M. Boll and E. Larsen, Acta Chern. Scand., 1969, 23, 2191.
C.T. Clarke and J.H. Jones, Tetrahedron Lett., 19n, 2367, and refs therein.
J .H. Brewster, Helv. Chim. Acta, 1982, 65, 317, and refs. therein; V. Ghislandi and D. Vercesi, Boll. Chern., Farm., 1976, 115, 489.
W. Marki and R.S. Schwyzer, Helv. Chim. Acta, 1976, 59, 1591.
T. Wieland, D. Schermer, G. Rohr and H. Faulstich, Justus Liebigs Ann. Chern., 1977, 806.
Y. Shimohigashi, M. Waki and N. lzumiya, Bull. Chern. Soc. Jpn., 1979, 52, 949.
7
A6
/1
Class 2a
H3CC":!CHZ~CH3
•
MCH
C:;
H3 CCHZCHZ
O HXai
N
H
~,
l.W)...coo 0
C H
. -.
/
2 5
2. (RH )2-m.lnyl-Sp
propylpiptluidine ,
tatrahydropyri dine.
C(Z)
f[2)
(6] [oJ
~
CII) [2J[S)
C(4)
4.
( - )nalo>
t
I
(-HEtOHY.
CU)
[7)
(6]
CI])
H
15. (R)-(-)S-molnyl-2-
( - ) pl/'Oidine
KI8. 12 .
(SH-)plpocoCie
acid A 10.7 . \
11I
piperidone,
H·l[$)
CHZCOOH
hexonoic acid
Au . .
_.- _ ._ .- - - - -_.- - -
2-eorboxylic acid .
- '- '- 'r ' - _._,_ . - - - --,- _.- - -'-' - '- '- '- '--'- ' - '- '- ' - '- '- '- ' - '.'- '- 'i
1
.
i
I
Ph
H+
R
12 .
hydroxyplpe,idine'
ocid .
Ph
(R)-(-)3,S - dlaminohexanoie acid All .le .
H
11. (2S,5R)-( )5 -
hydroJCy-6-mlthylpiperidine -2-carbcxyllc
(-).
, 13.
(R)-(+)olop
N=C/
'COPh
:
!
(RH-)phenyl «-(l-phonyl-
propyl1mino) "'nzyl kt ton.
14 . ( )N-(PWbl'6 -ylcorbomoyl l-
: R = C2H O)' Abs. X-roy ~/J.
(RH )phenyl a-(l-phenylo'
thyllmino) *zyl kotono
(R a
Ab• . X-roy
Ihroorino . Ab• . X-roy
CH,).
"'I-_.)~Jj.
_._, _._._.- -,- -_._--.- ._._._._.&.! _,_.__ ._._.__ ._. _._._._._._. _._.L...' ._._.(0.
_._.
_ , _._ ._._._._...L! ._
-.
(]
A' 14. 14 .
15. (S)-(+)5-molhyl2 -pyr r Olidon. .
(S )-(-) methylox;,one
. ,5.,15.
__ ._,_._._ ._. ____ ._. _._._._._
C(2)
H CAO)...CH COOH
3
,_~
(121
_.~O
(l
CI O)
p.ntonoic a cid
r'l
l.NI ~COOH
8 . (RH+)5-omiI1o- 10. (2S,5S,SS)-(+)5N-~n z oy l
i
....
HO·
H
tetra hydro- 2 · pyridon..
C
acid .
H3C~NI ~COOH
diominohe:.onoic: oetd.
r
/
/(4]
a. (RH-)S-molhyl-I,2,5,6-
7 . (3R,5RJ-( )3,5-
) 5-hydro'y-6mothylplpe,idino-2 - carboI
H0"'Y"'t
~
-
e. (2S,5R.6SH
co ---.....
''''~on,",
~~J
CH]
(SH+)4-om;no-
(Sl-(-)ilomc.tachydme.
AN.J.... " [2][.1]
o iCH]
H
".f' '",
CO : [tJ .
(l
~CH3
3.
(R)-(-)2-mol llylplperld.,. A10.15.
Mo
M.
H
,. (2R,6SH+)2-molnyl-S-
H •• ..
··C.....
I
3
2
~
18. (2S,6SH+)S-molhyllolro hydropyron- 2 -ylocetic
9
9
O~"
17. (R,Rl-H didosOlY pyronophor;'" .
ocl d . Mo ..Ior (+) .
CD of 2-substituted piperidines: [1].
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
J.c. Craig, S-Y.C. Lee, W.E. Pereira, H.C. ßeyerman and L. Maat, Tetrahedron, 1978, 34, 501.
RH. HilI and T. Yuri, Tetrahedron, 1977, 33, 1569.
O. Cervinka, A. Fabryova and V. Novak, Collect. Czech. Chern. Cornrnun, 1965, 30, 1742.
I. Kristensen, P.O. Larsen and C.E. Olsen, Tetrahedron, 1976, 32, 2799.
F. Kunz, J_ Retey, D. Arigoni, L. Tsai and T.C. Stadtman, Helv. Chim. Acta, 1978, 61, 1139.
A.V. Robertson and L. Marion, Can. J. Chern., 1959, 37, 829.
K-H. Michel, F. Sandberg, F. Haglid, T. Norin, RP.K. Chan and J.C. Craig, Acta Chern. Scand., 1969, 23, 3479.
See p. AIO.
D. Seebach and M. Pohmakotr, He/v. Chirn. Acta., 1979, 62 843.
A. Wägner, Acta Crystallogr. Sect. B, 1980, 36, 77.
I. Fonseca, S. Martinez-Carrera and S. Garcia-ßlanco, Acta Crystallogr., Sect. B, 1982, 38, 2735.
R Parthasarathy, J.M. Ohrt and G.ß. Chheda, J. Arn. Chern. Soc., 1974, 96, 8087.
I. Fonseca, S. Martinez-Carrera ana S. Garcia-ßlanco, Acta CrystalloJ(r., 1979, 35, 2643.
8
A
7"
Class 2a
~
~
~N)...CH
~ N~COOH
I
I
H
H
1. (S)-(-)1,2,3, 4'lllrohydro'
2. (SH+) 2· hydroxymelhyl·
quinolin.· 2-cor bollC'11 ic acid .
3
3. ( R)-(+ ) I, 2, 3,4 -
4. (RH+) I, 2 - dihydroqulnoli ne- 4 (3H)-one
tltrahydro- 2 methylqoinol ine .
1,2 , 3,4~tetrohydroqu i no lin • .
M. . .1" (+).
CH!
C:~H
I
H
HOOC +
morpholin • .
CO : [8].
•
propi onie acid .
CH!
Cut
o
Br +
[J']
H
COOH
S
' CH!
e. (SH+) 3 ' molhyl'
H
11. (S)-(-) 2'oni lina '
Ö
(5 ) -(- ) ."in.
A4.3.
~
[4]
C
COOH
H2 N+
(R )-{+) 2-brom.proploni<;. acid .
NJ.-- NH
(S )-!- )2-molhyla,ir ldint . A'14. 8
ORO/CO : [7] .
• (S)-(-)2-f(2-blnzimldaZolyl )rhiO)
propionic acid .
COOH
CH~CHPh
H
Ii:2N +
H
CH!
Br +
CH!
(S)-(+)olon.,..
CH!
H
B'+H
CH 20CH 2 Ph
8. (SH-)4-phonyl-
8. (S )-(-) 3-bonzyloxy2 - bromopropionie acid
3 - buten-2-omi ......
ALl'.
AI.14.
CH:!OH
10. (Rl-(-)2- bromo'
propan-I- 01
O" 2.
C,411 (rd
CI12'
~o]
-
HN~!yCH!
c
H2NlN~N)
[12J
I
H
( S)-( )3·omino·
I'butyne A'14.1.
11. (SH-)3-melhyl2,5 - dioxOpip.roline.
el2' ~(rl]
12. (SH-)6'melhyl5,6,7,6-1.I,atlydropterin.
oA
I-butene .
111. (SH- )2-rnelhyl'
piporOZinl .
d i· N · M.(+l .
I
N
MI
-
~yCH3
H+13-bonzy lolY'
2·bromoprapon+oI .
(R
)
CH 2- { )
~
CII '
H
te. (SH-I1!l,6,7,6·tltra-
(S)-(+ ) I, 2 ' diomino'
hydro·I,3,:i,6 · telra·
mlthyllumO" ne.
proponl A 18.'.
" CH!
17. (SH )4-mllhyl'2("nophthylmelhyl )
Imldazollnl
hydrochloridl (-) .
P.S. Portoghese, J. Pharm. Sei., 1964, 53, 228.
A. Fredga, Acta Chern. Scand., Sero B, 1977, 31, 869.
W.L.F. Armarego, B.A.Milloy and W. Pendergast, J. Chern. Soc., Perkin Trans. 1., 1976, 2229.
See p. A4.
Y. Yamamoto, J. Oda and Y. Inouye. J. Org. Chern., 1976, 41, 303.
L. Maat and R.W. Wulkan, Red. Trav. Chirn. Pays-Bas, 1981, 100, 204.
G. Bettoni, C. Franchini, R. Perrone and V. TortoreIla, Tetrahedron, 1980, 36, 409.
B. Ringdahl and R. Dahlbom, Chern. Scr., 1977, 12, 47.
W.L.F. Armarego, P. Waring and J.W. Williams, Chern. Cornrnun., 1980, 334.
W.L.F. Armarego, H. Schou and P. Waring, J. Chern. Res. (S), 1980, 133.
S. Matsuura and T. Sugimoto, Bult. Chern. Soc. Jpn., 1981, 54, 2543.
T. Sugimoto and S. Matsuura, BulL Chern. Soc. Jpn., 1980, 53, 3385.
D.D. Miller, F. Hsu, R.R. Ruffolo and P.N. Patil, J. Med. Chern., 1976, 19, 1382.
A. Lindquist, B. Ringdahl, U. Svensson and R. Dahlbom, Acta Chern. Scand., Sero B., 1976, 30, 517.
9
N
~
[tJ']
N
1. M.P. Paradisi and A. Romeo, J. Chern. Soc., Perkin Trans. 1, 1977, 596.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
13.
H
\
C ~ (tJ']
0
MIN: ] :
14. (SH+)3'amino-
111
A
8"
Class 2a
CIS)
-
CH 2CH,.OH
H~+H
HB,
[2]
1. (S)-(
(S}-(+)2-ominopenlonaie acid A 10. 111.
)6-aminan on-2·one.
hydrac~lOr id8 (+).
.............J.J)
CH:!CH:!CH 3
4. (SH+) 3 - ominoll•• on+ol .
5 . (SH ) ' - bo-omo-3-
2_ (SH )6-omlnonon2 - yno KUe .
101- 10.yl (+).
" ..yla"""".
"ydrobromido (+) .
~
C( 2)-"""""""
CH=CH 2
H2N + H
H2N+ H
CH2 CH 2 CH a
!I.
CH2 CH:!CH a
CH:!CH:!CH 3
6. (SH-)3'Qmino'
( RH-)3·~exylami ne .
e. (S )-(+)3-amino-
7 . (S)-(-,.)3-amlno-
hex· I· yne.
CH:!COOH
he l!onoic acid .
l"Iu:-l-en • .
+
cU)
H,.N +
CH
=:CH
2
~
[~]
C=CH
H2 N + H
pentane .
+
(CH 2 ).COOH
H
C(4)
[6)
CH a
12. (SH-)6-omlno-
H
CH a
A U e.9.
N-pI1t"olimido (+) .
10.
C(4)
NH2
[7]
H:!N
+
H
-----w-
CH a
(5H-)4-ominopenlaooc
acid A' 14. 14.
N-phtholimide (-l.
(SH+)2-bulylami no
A' 14 . 2.
[9)
14. (S)-(-)2' llydrozinobutane .
111.
(5 )-(- )I -(dipMnylmelhyl)2 - (2 - buly l )dio,ene.
H
C 2Hs
CHzCOOH
H:!N +
H
CH a
-
CH 2CH20H
cm
[8]
H2N + H
CH a
13_
(5 )- (+)3-ominobulonoie
acid A 19.9.
101- p~lho li m i de . (+)
--- '- ',i
(SH+)3'aminobuton-t·ol .
CU~[8]
C~:'N
CH~
0'" "'0
(CH 2CH2C1)2
16. (2S,4SH+)4-methylcyclophosp"
1. W. Oppolzer and G. Flaskamp, Helv. Chirn. Acta, 1977, 60, 204.
2.
3.
4.
5.
6.
7.
8.
9.
Oz
I
C(4)
--
C2 HS
~+CONHZ
lA~/N
C(4)
CH a
H
H
11 . (S)-(-),,-othyl'I,2(S H+l3- aminob.n,ol~lozol. - 2 l 3Hl
pentonoic acid .
ocetomid' -I,I-dloxidl.
N-phthaUmi do (+).
CHzCHzCOOH
_
(S) - (- ) 5- amina " ••onoie
acid. N-pI1tha limid. (+) .
hip'onoic Qcid .
+
+
H2N
[6]
(5 H +) 2-aminobulyrie
acid A 11.13.
N-b.nz.... 50lp~ny1 (+).
N-pI1lha ll midt(-).
(CH2)3COOH
_
HZN
CI41
CzH s
(s H - ) 3-amino'
I-pentyno A'II.9.
9 . (SH+)3- omino+
_
[.J]
C2HS
~Hs
H~
-
CH2 COOH
C(2)
G. Habermehl and H. Andres, Justus Liebigs Ann. Chern., 1977, 800.
B. Ringdahl and R. Dahlbom, Acta Chern. Scand., Sero B, 1976, 30, 812.
B. Ringdahl and R. Dahlbom, Chern. Scr., 1977, 12, 47.
C.M. Svahn and N.A. Jonsson, Acta Chern. Scand. Sero B, 1978, 32, 137.
G. Lucente, G. Piccinni and A. Romeo, Gazz. Chirn. Ital., 1966, 96, 1380.
G. Lucente, G. Cagnetta, G. Fiorentini and A. Romeo, Gazz. Chirn. Ital., 1965, 95, 1335.
R. Kinas, K. Pankiewicz, W.J. Stec, P.B. Farmer, A.B. Foster and M. Jarman, J. Org. Chern., 1977, 42, 1650.
K.R. Kopecky, P.M. Pope and J.A. Lopez Sastre, Can. 1. Chern., 1976, 54, 2639.
10
Agil
Class 2a
H+~:20H
C~OH
--
H-f:
C(4)
[I]
C(C~l.
2.
I. (RH+12,3-opoxy·3·mothytbulon-l-oI .
(RH+13-moth~l
butone-1,2, 3- trial
, . (5H-1/.rl-butytthiiran •. CD 0', ond
(RH-13,~-dimo t h~~
butan.-I, 2 -diel .
8y AS (H1 [S).
A '_14.
Qf rtllat.d thiiron.,
[61
________________________________________________________ LI __________________________________________
_
(CH 2 )'OCH.
HO+H
C2 H 5
-
O+(CH21~OCH' =
MoLI
L-'J
I
!S.
··l...oAo
-
OC-(CH 2 1.
4. (RH+1undocy loxironf_
(5H +1tolrodocon~'ol A " . , ' _
("'"'l
H.C(CH 2 11O
(RH+15·hyd
acid lacton. _
----------------------------------------------------------------------T·--------------------·-----------------COOH
H°tCOH
H"II--t - H
~
o
Hb
[~
0
(C~l.CH.
(5)-(- )2'om,nopentonoie acid
AI0.8.
O-erythrofuronose
8. (5)-(+ )3-hydroxy -
(5)-(+12-hydroxy'
hexanoie acid.
2-heptonone
Al.24.
Cl.II .
Y"lI.
7. (5H 13· hydroxy 2,3-dihydrofuran_
-------------------------- --------------------------- ------------- - __ ____ J. __ ------T------ -------------- --- -----
oo~
Ho ··lo~CHi>H
CI- O-goloctopyronose
A 18.17.
r
MoO"
0.
0
CH;,OH
". 0.
~
MoO"
8. (25,SSl-(-)6-hydroxym.·
thy l'2-mlthoxy- 5,6dihydro- 2H- pyron _
0
CH;,OH
:
". (25,65 H+16'hydroxy '
CHO
methy l- 2 - methoxy·
CH
I
CH:z
CH:zOH
tetrohydro pyro n.
----------------------------T--------------- ---T---------- --
Ht~)Ph
H$OH
H
OH
H
OH
---------
111
H.
~
O
o
"CH2~Ph
I ".
:
10. (RH ) Qerm,Chrt,sone_
Ab._ X·roy ~Oj.
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
11. (RH+1ovelloneol.
8y AS (H) [1/]
12_
(5)-(-)l,7-bi.(~,4 -
(R1-(-12-(bonzo~loxy
methylltelrahydrofuroo _
i
dihydroxyphonyl)- 5-hydro,y3-hflptonone . Ab'. X-roy ~2J.
S. Yamada, T. Mashiko and S. Terashima, J. Am. Chern. Soc., 1977, 99, 1988.
P. Dumas, N. Spassky and P. Sigwalt, Makromol. Chern., 1972, 156, 55.
J.L. Coke and A.B. Richon, J. Org. Chern., 1976, 41, 3516.
M. Masada and K. Nishimura, Chern. Lett., 1981, 1333.
J.P. Guette and N. Spassky, Bull. Soc. Chirn. Fr., 1972, 4217.
G. GottarelIi, B. Samori, I. Moretti and G. Torre, J. Chern. Soc., Perkin Trans. 2, 1977, 1105.
R.E. Ireland, C.S. Wilcox and S. Thaisrivongs, J. Org. Chern., 1978, 43, 786.
A. Konowal, J. Jurczak and A. Zamojski, Tetrahedron, 1976, 32, 2957.
J. Cleophax and S.D. Gero, Bull_ Soc. Chirn. Fr., 1967, 1441.
H. Noguchi, U. Sankawa and Y. Iitaka, Acta Crystallogr., Sect. B, 1978, 34, 3273.
L. Ananthasubramanian, S.T. Carey and M.S.R. Nair, Tetrahedron Lett., 1978, 3527.
T. Suga, S. Ohta, T. Hirata and T. Aoki, Chern. Lett., 1982, 895.
11
14. (RH+)2-(bonzoyloxymOlhyl )-2,5'
dihyd
A
1011
Class 2a
CH2PPh2
Me2N+
C~CH2COOH
H
H2N +
~
[2)
H
PhC~-()
N
I
CH 2Ph
C~Ph
1. (S H+)pllepllo,
2. (R)-(-) 4 -omino- 5 pheny lpenlcnolc oc.id .
3.
pyrrolidine.
~COOH
----wHCHO
(S)-(- )p/lonylalanine A ~ .1 2 .
~ . (SH - )2,~-dihy dr oxy -
phen'llo lanine .
H
4 . (RH-) 2- bonzyl-
(RH+ ) 5-ben,yl -2-pyrrolidoo,,-
~NH
--
~NH
o
o
1.
8_ (SH-) ',2,~,4-t.tro
CC!COOH
~COOH
C(3)
(.,]
e. (S H+)3,4-dihydro-
( S H+)~-CQ rb o.y
dihydroisccorbosty,.i 1.
Me o.lor (+).
hydroi soquinoline- 3,corbox)'lic acid ,
isocoomorm-3carbo:.:ylic acid.
N-benzoyl(-) .
~CH2COOH
~NH
C(31
r;]
9 .§OR ,91?)-(+)t~ -met hyl10. (SH+)3-oorboxymethyl3,4-dihydrocorbo.ly,il
13 -ozotricyc lo [7.3 I. 0 2 • 7]
trid.ea-2 ,4,S-trien-I'-ontl _
Me ester (+ ) . N -Me (+ ).
12. (SH+)3-hyd,oxymethyl-
11. (S H+)!I-ominomol hyl2-mel hyl- 3,4-di hyd,o-
2-melhyl - 3,4-dihyd'ol. ocorbosty'iI. O-Ac(+) .
caroostyrd,
,'-'-'-'-'-'-'-'-'-'-'-'-'-'-'-
i
i
(SH-)!I-hydroxymelhyl1, 2 ,3 1 4 -tetrahydrOiIOqulnoline A 5 . 16.
N-tdoH.
-'-'-'-'-'-'-'-'-'-'-'-'-'-'-'T'-'-'-'-'-'-'-'-'-'-'-
I
--
I
C(2)
~s]
I
13 _ OR,9S) : (+) I~- m"hy l- 2 7 i 14. (S)-(+)N-hydroxy1~-QZOI"OYtlo[7 ,3 I 0 • ] i
omphetomine.
tndeea-2,4,S- tn.ne .
(S H+)omp/letomine A!!_ 10
Ab • . X-roY[9J.
i
I~. (S H+)2- I.ocyono
I - p/lonylp ropone ,
N~N- di -Me (-).
Abs. X-roy ~O).
.
18. (S H+) 4 -phenyl2 - boty lamine .
Ab• . X-rtJy ~21
-_._._._._._._._._._._.1._'-'-'-1'-'-'-'-'-'-'---'-'-'-'-'-"'-'-'-'-'-'-'-'-'-'-'-'-1'-'-'-'..1·_·_·_·_·_·_·_·_·_.i
i
i
MoO
C)vNHCOOS02NH2
N
I
Et
17. (S)-(-)sulpi,ide. Abs. X-roy ~4J
i
I
I
i
CQOH
'<:::
HO,lj
QH
NH
CH2 ~
dD(H
90
••
~
OMO
2
3
OAt
00
--N~I
OM I
OMo
19. (2R,3R,4tJR,90RH-l
2-00.loxy- 3 - t,lmethyl-
18. (S )-(-)5,7-dihydroxy- l )t,2, 3, 4 - t.tron ydroi~oCluino !in • .
Ab • . X-roy ~~ .
(3,4J~·trim. thox)'b. nzyl
ammoniodecalin iodid • .
!
Alls, X-",y ~61.
ii
i
20. (R H+)2-dipropylamino5- hydroxylet,olin .
Ab," X-roy ~71 .
I
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
T. Hayashi, M. Fukushima, M. Konishi and M. Kumada, Tetrahedron Leu., 1980, 79.
e.e. Tseng, S. Terashima and S. Yamada, Chern. Pharrn. Bull., 1977, 25, 29.
R. Buck, J. Eberspächer and F. Lingens, Justus Liebigs Ann. Chern., 1979, 564.
G.E. Hein and C. Niemann, J. Am. Chern. Soc., 1962, 84, 4487.
S.G. Cohen and R.M. Schultz, Proc. Natl. Acad. Sei., USA, 1967, 57, 243.
H. Kato, E. Koshinaka, T. Nishikawa and Y. Arata, Yakugaku Zasshi, 1974, 94, 934.
T. Wakabayashi and K. Watanabe, Tetrahedron Leu., 1977, 4595.
K. Watanabe and T. Wakabayashi, J. Org. Chern., 1980, 45, 357.
H. Herbert, Acta Crystallogr., Sect. B, 1978, 34, 611.
D.G. Hay, F.J. Leng, M.F. Mackay and B. Ternai, J. Cryst. Mol. Struct., 1977, 7, 59.
B. Lindeke, G. Anderson and U. Paulsen Acta Chern. Scand., Sero B, 1976, 30, 789.
P. Murray-Rust, J. Murray-Rust, D. Hartley and J. Clifton, Acta Crystallogr., Sect. B, 1982, 38, 306.
M.P. Periasamy and H.M. Walborsky, J. Am. Chern. Soc., 1977, 99, 2631.
L.Y.Y. Ma, N. Camerman and A. Camerman, Acta Crystallogr., Sect. B, 1982, 38, 2861.
K. Yamada, M. Takeda, N. Itoh, N. Umino, K. Ikezawa, A. Kiyomoto, K. Aoe, K. Kotera and T. Iwakuma, Chern. Pharrn. Bull.,
1982, 30, 1588.
16. B. Lee and G.M. Henry, Acta Crysta/logr., Sect. B, 1976, 32, 938.
17. J. Giesecke, Acta Crystallogr., Sect. B, 1980, 36, 110.
12
A
11 "
Class 1b, 2b
H,
P03~
~
H : •. :
[I]
Ph
P~H2
H+Ph
NH
Ph
N~
~C-f;H
2 . (RH+) cminoph.nyl-
(T)
Ph
methonesulfenc aCid
I
I
1. ( ) RBIX-roy[l ).
CS
N
CII )
H,C+H
Ph
H,C +
Ph
4.
(S )-( - ) I-phenylet hylcmlne A 19. 14.
( S,SH+)N,N~bi.(a
~ . (S,SH +)N,N'-bIS'
phenylethyl )thioureo
(o -phenylethy l)
corbodi 'mid• .
( 1- phonylothyl)
ketlnell'T\tne
He ,
•
3. (S H - )di phonyl-N-
H
Ph
C
11
N
[4)
H,C + H
(4)
11
~
NH
NH2
(2)
H + C H3
NH
C
X
Ph
H+CH,
NHZ
H,CCH 2 CH Z +
H
Ph
6 . (S )-(-) I-phenyl·
butylamine.
7. (S)-(-)I'phenylelhyl
i50cyono te .
: 90
-'- '- '- '- '- ' - ' - I - '- '- '- '-'- ' - ' - '- '- j- ' - - ' - ' - ' - ' - '- ' - '-' - '- ' - j - '- '- '- '- ' - ' - ' - ' - '- '- '- '-
2
"""OM.
101.0
HO
(tz
i
(N)
z
H
H,
~
N
U
H
i
tH2
HO ± H
H
@
U OCHZCHzNMeZ
""N
00101.
0101.
I ~
11. (-) eiro modol.
Abs. X-roy (~
8 . ( IS,3S)-( )3-di.lhyl-
amino· '·(2,5-dime thoxy
phenyl) bu ton+ol .
Abs. X-roy [6].
8 . (S)-H2-[4-(2'hydroxy2- (.3,4 - dimethoxyphenyl )
ethyl t-",perozinyl' 2, 4,S-
J
10. (S)-( )corbinoxomine .
Abs. X-roy [8J
c:yeloheptofnen - I-one
Abs. X-roy [7}
1. T. Glowiak , W. Sawka-Dobrowolska, J. Kowalik, P. Mastalerz, M. Soroka and J . Zon, Tetrahedron Leu., 1977, 3965.
2.
3.
4.
5.
6.
7.
8.
9.
K. Lee, N. Horowitz, J. Ware and L.A. Singer, J. Arn. Chern. Soc., 1977, 99, 2622.
O. Cervinka, V. Suchan, O. Kotynek and V. Dudek, Collect. Czech. Chern. Cornrnun ., 1965, 30, 2484.
O. Cervinka, V. Dudek and V. Senft, Collect. Czech. Chern. Cornrnun., 1978, 43, 1087.
N. Furukawa, M. Fukumura, T. Nishio and S. Oae, J. Chern. Soc., Perkin Trans. 1, 1977,96.
Y. Masuda, Y. Iitaka and H. Hamano, Bull. Chern. Soc. Jpn., 1974, 47, 825.
F.R. Ahmed and J. Bagli, Can. J. Chern., 1982, 60, 2687.
V. Bertolasi , P.A. Borea, G. Gilli and M. Sacerdoti , Acta Crystallogr. Sect. B, 1980, 36, 2287.
W. Stallings and J . Donohue, J. Cryst. Mol. Struct., 1981 , 11,59.
13
A
121f
Class 2a, 2b
,~f~
C~NMO~Cle
2. (2S,3SH-)2,3-
1. (-)onthopleurino .
dimothylthilron .
;So (2S,3SH-)2,3-bi.
(diphlnytpho5phino)
4_ (R)-(-)3-hydroxybutan-2-ono .
~:~;"~I
,~ r~
H~:H
H O TH
'~
CH2Ph
CH2NH2
(2R,3SH+)4 -omino2,3-dihydroxybutyrl<
acid A 24.11.
"-[I]
f:. ,:
H
OH
CH3
7. (SH+) 4,4 '-dimothyl'
(2R,3R)-(-) butone-
D. (2R,3SH+)1,4diphln ylpho5phi no
8. (1S,2SH+)t,2-di-2-
2,3-diol A ;S.7.
2 , ;3-diol
pyridylothone-l,2-diol.
Mnzoin ,Other 4,41•
disubstd . benzoins: (4].
C(~l [2]
C(9)~
---
--w- AC~+~AC
l4J
e.
(2 R ,3RH+)
(lS,ZS)-(- ) 1,2-
(2R ,3R)-(-)dimethyl
cliociltoxy suc:cinote.
diphenyltthon.-
tarterie ocid
10. ClS,2SH-)1,Z-bi.
A 2.6.
MeodMe
C1t2)
[3]
I
Mo
11. (3S ,4S)-(+) 3,4H SC(CH 2 )g'
~..-
HO
H
=t=
0i20H
H
KOH
H
--tJ-
OH
C~OH~
1C~)4CH(CH3)2
(7R.8SH+)7,8-opo.y-Zmothyloctaclocone (di.potluro)
Y'S.S.
(ZR.3R)-(-)butone-
(t1
l,2-diol
A 2S.11.
MX
dlmethoxytetrohydrofuron.
,~
!P1l
'O~
~/l
f:
0
0"
H
CH2
_0/"
/'H
KOM
'; r:.
CH~H
~X
14. (2R,3RH+)1.4 -
1.
dihO!Obutane-2 3dioh(X~CI,Br
~C~
12. (S,S)-(+)bioxirane O,Z: 3.4-diepoxybulone) .
1,2,3,4-tetrool
(0- throi lol) CI . 10_
o
13.(3S ,4S)-(-) 3,4-
(p-tayl lethone- t,Z ~~ Otherp-5ub.ld.
~
~d" [41
l[!I]
N
MOOdO#oO
Ph
COOM.
dimethoxythiolon.
dlrnethoxy·'m. thylpyrro lidin..
H~+~H
C(3)
C
C'~)
[.l']
8. §(3R,4R)-(+)3,4-
Ph
COOMe
1!1. (ZR,3RH+) 2,3dibromobutone-I t 4dia 0" 2 .
'-o~(t~
'; f::
KOH~
C~OH
16_ (2R.3RH+)Z.3diChlorobutcna-I,4-diol .
1. J.A. Musich and H. Rapoport, J. Am. Chem. Soc., 1978, 100, 4865.
2. R.K. Hili and T.F. Bradberry, Experientia, 1982, 38, 70.
3. D. Seebach, H. Kalinowski, B. Bastani, G. Crass, H. Daum, H. Dörr, N.P. Dupreez, V. Ehrig, W. Langer, C. Nüssler, H. Oei
and M. Schmidt, Helv. Chim. Acta, 1977, 60, 301.
4. M. Imuta and H. Ziffer, J. Org. Chem. 1978, 43, 3319.
5. K. Mori, T. Takigawa and M. Matsui, Tetrahedron , 1979, 35, 833 .
6. M. Imuta and H. Ziffer, J. Org. Chem., 1978, 43, 3530.
7. J.J. Plattner and H. Rapoport, J. Am. Chem. Soc., 1971, 93, 1758.
8. R.H. Biom, J. Am. Chem. Soc. , 1945, 67, 494.
9. M.D. Fryzuk and B. Bosnich, J. Am. Chem. Soc., 1977, 99, 6262.
10. M. BucciareIli, A. Fomi, I. Moretti and G. Torre, Tetrahedron, 1977, 33, 999.
11. P.W. Feit, Chem. Ber., 1960, 93, 116.
12. I.R.K. Ness, H.G. Fleteher and C.S. Hudson, J. Am. Chern. Soc., 1951 , 73, 4759.
14
A
1311
Class 2a, 2b
CH 3
H + NH 2
COPh
I. ( 4S,5R)-(- )4''''ethyl - 5 - phonyl-2o,olalidon • . N - Me (- ) . CO : [I).
"
H
~C •. ( N y O
Ph'"
0)
-
cy ". \
C12)
H4NH2
[2)
HToH
~
[6J
,
:+~::OH
TPh
[2]
CH 3
H~NH2~
[2]
H~NHC9
CCH20 T
Ph
-
5. ( ~5 ,6s)-(+)~-m.lhyl - 6- ph.ny l -2 -
om;no- l -phonylP"'!>on-
(l5,25)-(+)2-om;noI-p/lenylp.-opon-I - ol
<"' - norephedrine ,cothiM)
m",pholono . N - Mo(+) . CO : [I).
A 21. 11 .
N -Mo =" (-)ephedrine
A21.10.
' - -- -_ . _ . _ . _ . _ . _ -- - -
- -- -
- - _ ._ - -- -- -- -- _ . _ . _ - - -- -- -- -_ . _ . _ . _ ._ ._ -- -- -_ . _ .-
Ph'_.(~) - [H] Ph""(~fO Ph" °
[4]
Ph" °
[4J
cl2)
! 8 . ( 2R,35)(- )2 , 3'
! dipheny l morphol'lne.
H
Ph
1-01 (norephedrine),
7. (25,35H - )3-hydr o.y- I
2-methy l- 3-phonyl-
/
CH3
H O TH
5. (lR,25)-(-)2-
6 -phenyl - 2 -morp holon • .
N - Mo (- ). CO : [I]
propionic aci d .
COCI,/
( [3]
~
4. (55,6RH - )5- molhyl-
CH 3
(cothinone ).
[~]~[H]
[2]
COC1:r " ' "
3. (4S,5SH+)4-methyl- 5-p/lenyl-2'
O'Ololiden • . N-Mo (+l. CO : [ I).
2 . (5)-( -),,-cminopropiophenone
9 . ( 55,6R )(- ) 5 , 6di phanylmorpholin
r
Ph
H=F NH2 CCCl,
H
OH
-
[4)
Ph)-NH
ph"",_rO
°
Ph
(lR,2S )(- ) 2-amino2-diph4!lnyl ethon~
10. ( 45,5 R H - )4,5-
Ph
PI>,
"
d,phenyl - 2-oxozolldone .
!
CO : [ I).
3 - ono _CO : [I).
A20.14 .
CO : [I).
_ __ . _. _ __ __ __ __ . _ _ .J ._ ._ __ __ _ __ __ __ __ ._ ._ ._ . _ - -- --- -- -- .- .- .- -- -- -- -- .- .-.- -- -- -- - -- .- .- .- - -- --
' N)
X
Ph °
11. ( 25,35)(-)2,3diphenylmorpholine .
111
'
X
H-+-- 2
H
H
Ph
Ph
Ph
12.
NyO
NH
HO+H
0)
j-NH
Ph~_rO
°
Ph
( ~S ,6SH-)~,6-
(l5,25)(- ) 2'o"'ino-
dipn.enylmorpholin-
' , 2 - dipn.enylethanol
HI. (45,55 )-(-)4,5 diphenyl - 2-oxozolidonf!l _
CD: [I).
3-0n0_ CD : [I).
A 20.14 .
CD : [I).
L _ __ __ __ __ __ ._ ._ ._ ...,. _ . _ . _ __ __ __ __ ._ . _ . _ . _ ._ . _ . _ __ . _ ._ - - - .- -- - - - - - -- .- -- . - . - -- .-
Ph
Ph
cUl
~ HOH2C
14. (4R ,55H- ) te,rohydro4 ,5-diphonyl -2-0.ozolono .
T
H - t - NH2
H
H2N- + - H
HOHzC-t-H
Ph
cW
~ O~C T H
Ph
Ph
(25,3R)-(- )3-ornino2,3-d;phenylpropon-I -ol
443.13.
( 25,35)(-)3'
omino-2,3 di pnenylp.-opon-I-ol A43. 2.
a
)ONH - t - H
Ph
1!1. (45,55)(+)tolrohydro-4,5-diphe nyl2-Q)(ozolonll .
1. W. Klyne, P.M. Scopes, N. Berova, J. Stefanovsky and B.J. Kurtev, Tetrahedron, 1979, 35, 2009.
2.
3.
4.
5.
6.
G. Fodor, J. Stefanovsky and B.J. Kurtev, Monatsh. ehern., 1967, 98, 1027.
X. Schorno and E. Steinegger, Experientia, 1979, 35, 572.•
J.N. Stefanovsky, S.L. Spassov, B.J. Kurtev, M. Balla and L. ütvös, ehern. Ber., 1969, 102, 717.
G. Fodor, J. Stefanovsky and B.J. Kurtev, ehern. Ber., 1965, 98, 705.
C.H. Heathcock, C.T. White, J.J. Morrison and D. van Derveer, J. Org. ehern., 1981, 46, 1296.
15
A
1411
Class 2a, 2b
x
:~:
W,..Ph
0
X
Ph
ph,nylethone- I .2-diols
( X: CI(-),
x: Me(+).
3 - phenyloxlrOnes
ex = CI, Mo).
"~~-H--~-;i-Ph
2-phonyl.,hono -I, 2diol. ( X = CI,MI).
\ ' Ph
Ph
A'
coOX
H+OH
(R)-( +)phonyl -p ' Iolyl-
4 . (RH+)phenyl -[3Cl-phenyl-I,2,4 -I,io,0Iyl)J
phenylox irane s
(X : CI ,Me) _
co rb lnol A I 1e . 11 .
corbinol. Ottler
,imilor compds : (2 J.
--
CU )
C( 5)
[I)
Ph
8. (R )-( -)4-chlo,o-
!!. (lR, 2R)-(-)I-o'yl-
Ny N
HIOH
3 . ( 2S,jR)-H2 - oryl-3-
2. Cl 5,2R)-(-) I-o
1. (2R,3"1)-(+)2- o'yl-
.6
1/\
(R)-(+)mondllie acid
A21 . 12 . ilrilo (+)_
benzoin ( X = CI).
(Rl-{ -) 4-mer ylblnzoin ( X = MI).
11.
1. (R)-(- ) 2-cycloh.. yl·
2-hydroxyocetlc: acid .
(RH+)cyelohnyl'
p- Ioly Ico'blnol.
[,J
CI1I
$ . (IR,2R)-( ) l-phonyl-
propone-l,2 J 3- triol
2,3-0- i sop'opylideno (-).
(R)-(-) I-phonyl.thone-
1,2-diol
A22 . 13.
(R}-(-)2, 2,2 -
10. (5)-(+) I-,,_ylprop'
2-yn-l-01' D" 3 .
"'l '-J
[oV
l
y ' (4)
11 . (R)-(-) Hl·nopllthyl)-
tr1 luoro-I-pne.nyl -
~l'-J
etraonol
A22 .18
2,2,2-trlfluOroli thonol .
~
Chirol nmr
Hz. " ' .
[S]"'-.
CH=CH 2
H-t:~H
H+OH
~~"""
13 .§(5H-) I-phonyl'
p
(5 )- (-) 1- phenylproponI - a l A' 18 . 14.
CF,
~;;
Ph
Ph
/
,,, . (RH-)H9' onth'yl )2,2,2- tri fllJoroethOtlol.
- ._._--.-.- . _.- ....,
12 . Cl S,65 )-t+-)1, 6-diphenyl-
j
r
._.-.--- . -.-.-.-.---.-.
- ·-·- ·- ·-----·-·l
hu:o-2,4-diyne-I.6-diol. !
L.._._. _._._ ._._ . ___ ._._._ ..J
COOH
HO+H
CH 2 Ph
-
(5 )-(-)2-hyd'oxy' 3phonylp
C. .... I .on,
1(9)
i
C(3)
~I)
" . (5 )-(-)2-hyd,oxy-3'
phenylproplophenon. .
16. (2S,3R)-(+)2-bon zoyl'
3-p",nyloxlronll
17. (R)-(-)2,2,2 -I, llluo,o'
I -phenylathy lamine
(cl'lalcooe epoxide).
A3.'
t Confusing use of D,L-convention and unclear stereoformulae in reference 4; these assignments are based on the statement in
reference 5 that the AC of A"14.10 is weil established.
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
J. Capillon and l-P. Guette, Tetrahedron, 1979, 35, 1801.
l.K. Fraser, D.G. Neilson, K.M. Watson and J.W. Heatlie, J. Chem. Soc., Perkin Trans. 1, 1977,646.
P.M. Dansette, H. Ziffer and D.M. lerina, Tetrahedron, 1976, 32, 2071.
I. Iwai and K. Tomita, J. Pharm. Soc. Jpn., 1960, 80, 160.
R. Weidmann, A. Schoofs and A. Horeau, Bull. Soc. Chim. Fr., 1976, 645.
U. Kuffner and K. Schlogl, Monalsh. Chem., 1972, 103, 1320.
See p. A22
W.H. Pirkle, D.L. Sikkenga and M.S. Pavlin, J. Org. Chem. , 1977, 42, 384.
W.H. Pirkle and l.R. Hauske, J. Org Chem., 1977, 42, 2436.
M.H. Delton and G.U. Yuen, J. Org. Chem., 1968, 33, 2473.
B. Marsman and H. Wynberg, 1. Org. Chem. , 1979, 44, 2312.
16
A
15"
Class 2a, 2b
(H3C~CH-(")
N
(H3C )2CH
I
H
(RH+) 2- i$Opropylpyrrolidine AI e . 10.
V
O
I
H
2.
1. (RH + ) 5 - isopropyl- 2 - pyrrolldono .
3.
(RH+) 4-amino-5-
methy lhexonoic aci d.
(S H+)2- omino-l(d iphenyl p hosph i no)3 ~methyl
~
[6)
butane
(valphos) ,
ClI)
CHPh 2
HO+H
CH (C H3 )2
4 . (.5)-(-) I,I-diphonyl- 3methylbuton-2-oI.
COOH
2
HO +
: H
C(2)
HNOI
C(~)
H2N+ H
CH (CH3 ).
C/OH)(CH 3 )2
!I. (5)-(-) 1,I-diphenyl-
§ (S H - )2-hydro,y-3-
!-methylbutone-
§ (SH-)voline
methylbu lo noic acid
1,2 - dioL
4' 4 .6 .
+
CII)
~
5J c(,1
C(2)
[5J
H2 N
CH (CH 3 )2
~
C~;;.:.-
HOH 2 C', (O
>--Ph
o
10 . (2R . 4S H+) 2·phonyl I J 3-dio;IColon- 4-yl -
mothanol (1, 2 '0-
b.nz yli de ne9Iyc.rol ).
CD : [7].
1.
2.
3.
4.
5.
6.
7.
8.
:.
•
'
+
Ph
H
C(2)
.--
[ I]
meth yl -I-phen ylpropcne . N -AcC-).
[8!
11. ( 2R,4RH )2- phonyl-
CH 20H
aldehyde 0 ,2'0boolylldoneglyeeraldehyde)
441.7
'
d,m4ilthy l-2 ,3-dihyd r otur an .
(H) ~
)-Ph {6]
0
12 , t2 S,4RH )2-phenylcorbo)(alde ~de
O. Cervinka, V. Dudek and L. Hub, Collect. Czech. Chern. Cornrnun., 1970, 35, 724.
C.c. Tseng, S. Terashima and S. Yamada, Chern. Pharrn. Bull., 1977, 25, 29.
1.1. Oh-Hashi and K. Harada, Bull. Chern. Soc. Jpn., 1966, 39, 2287.
J.P. Vigneron, M. Dhaenens and A. Horeau, Tetrahedron, 1977, 33, 507.
G. Li Bassi, P. Ventura, R. Monguzzi and G. Pifferi, Gazz. Chirn. Ital., 1977, 107, 253.
R.M. Carman and J.J. Kibby, Aust. J. Chern., 1976, 29, 1761.
R.M. Carman, C.J. Hawkins and J.J. Kibby, Aust. J. Chern., 1977, 30, 2465.
H. Redlich, J. Xiang-Jun, H. Paulsen and W. Francke, Tetrahedron Leu., 1981, 5043.
17
(5 )-(+) 3'mothy l- 2ptl enylbutyric Ocid
9 . (S)-(-12- .. opro pyl-2,5C
'j ,3 - dloxolon-4-
1t 3· dit"1(olan-4 -carbox-
H
CH(CH 3 )2
_
OHC •.: .~_ ~(
.. ,o
H • _' OH
' .. '
,-( > --Ph
o
HOOC +
CH(CH 3 )2
OH
H
[IJ
8 . (SH-) l 'amino-2'
c
H
HO
hydro, y -~-me lhy l'
butanoie acid ( AI·
hydroxY lioline ).
N- b.nzoyl (+).
Ph
H
7. (5 H-)2-hydraz ino-3 me thyl butonoic ocid.
c
r
A 4 . 19 .
COOH
H2NNH
6 . (S H+)2- amino-3-
HOCH
"Cr
2
Ph
13. ( 2S.4 SH + ) 2-phenylI) 3-dioxolon-4- ),1methanol. CD ; I?] .
A1611
Class 2a, 2b
Cl
HO
HO + H
~
CH 3
CH3
C~
ethonol.
ethonol.
~~
HO+H
2 . (S)-(-)2-(4-pyrldyll'
1. (SH-)2-(3-pyridyll-
HO
'","
H
[/J
C(Z)~
/[.1]
C(3)l[/]
C(3)
propan.~I.
[I]
pyridyl )"Ihanal.
(YH
3
N
I
CH 3
(I -'<,2S)-(-) I ·
ocld AI. 8.
C(5)
4. (2S ,6S H )4'oxaheplonl'
2 , 6-dial .
H
6. (SH+)2-mothyl'
morphoHn• .
/
C",J[6]
1
[2]
CH3
. .:-.
~[81
('o-(CH l
CI') \
CH 3 \
11 . §(S)-(- )2-( 2'
Rlploclll9 ;
'14.17.
2 - diol.
HO~: +--[~4]~--~:~~ ~j;. :
C(3)
H_
CH 3
3. (S)-(-) I,I-diphonyl'
Ce: ,5
~
-'CH l
7. (8S,12S }( )8,12-dlmllhyl-5,6,8 9,11,12,14 ,15-oc:lohydno [b]blnzo-l,4,7, 10, 13 -pentQolCo ~
cycloplntodecin.
SH
e~H
HOOC+H
:
CH3
CH 3
proplonl c: acid
A
8 . (5S ,7S )-(-)7-mllhy l-l, 6-dioxosplro (4 . 5J deCOM.
(1S ,2S )-(+) 1phlnylpropooe1,2-dlol A21 . 2 .
(-'<)-(+)2- morcopto-
8 . (3I1,6S)-(- )
12.10.
, ' -'-'-'-'-'-'-'-'-'-'-'-'-'-'-'-'-'-'-'-'-'-'-'-
i
-
I
CH 3
H+
COOH
SI
H+
~
HOOC+H
COOH
CH)
~
SI
HOOC +
H+COOH
co
So
l
[7]
H
i
I
C2H,
11. (R,IIH+) 2 , 2 'dislltlnobisproponoic
acid.
I
i
So
l
HOOC+H
CH 3
10. (R,R)-(+)2,2'dithiobisproponoic
a cid.
I
~~
CHl
C(I)
[/2]
(R)-(-)cyslolnl
A 4 .11 .
13. (2R,4R )- ( )2-p-lolylthiozolidin. - 4 -
corboxylit ocid .
!
di~,"nobisbutQnoic
I
I
acid.
!
12. (R,RH+)2,2'-
Abs. X-r"y ~~ .
COOH
_._._.-._._._._._._.-.-.-.-.-.-.- .-.-._._._._.- - '- ' - '-'-'--'
COOH
H2N + H
•
~~)
CH~CH2
14,
(S)-(+)2-ominobol-;3_
oc:ld.(vinyIolyc,ne).
COOH
HzN+H
•
CHzCHzSMI
(S)-(-)m.lhlon ....
A 8 .17.
;~] .
I
COOH
!
H2 N + H
HzN;r-H
18, (2R ,4R)-(+) 2- (2-hydro.yphenyl)- ;3-(3-morcoplopropionyl)thiozo5dine -4-corbollylic: acid.
Abs. X-roy ~4) .
CHzCHzSIMI
111. (S)-(+) .. llnomolhioninl. I
I
i
CH 2
I
I
S
CH z
H3C + H
COOH
17. (2R,6SH )-2-omino6-molhyl- 4-lhlahoptOMdioic acid (2-carboxypt'opylcy .. t.in. , .
(2R, 4R)-ilomor 0100 [><&pd;
'e' tonlOs not ckJrified VJ'J.
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
M. Imuta and H. Ziffer, J. Org. ehern., 1978, 43, 3530.
H. Nitsch and G. Kresze, Angew. ehern., Int. Ed. Engi., 1976, 15, 760.
J.P. Vigneron, M. Qhaenens and A. Horeau, Tetrahedron, 1977, 33, 507.
R. Zioudrou and P. Chrysochou, Tetrahedron, 1977, 33, 2103.
K. Hintzer, R. Weber and V. Schurig, Tetrahedrun Lell., 1981, 55
See p. Al2
B. Ringdahl, J.c. Craig, A. Fredga and W.A. Bonner, Acta ehern. Scand., Sero B, 1981, 35, 467, and refs therein.
M.O. Mack, R.R. Hendrixson, R.A. Palmer and R.G. Ghirardelli, J. Arn. ehern. Soc. , 1976, 98, 7830.
G. Bettoni, C. Franchini, R. Perrone and V. TortoreIla, Tetrahedron, 1980, 36, 409.
A. Afzali-Ardakani and H. Rapoport, J. Org. ehern., 1980, 45, 4817.
J.C. Craig, S.c. Lee, G. Zdansky and A. Fredga, J. Arn. ehern. Soc., 1976, 98, 6456.
R. Parthasarathy, B. Paul and W. Korytynk, J. Arn. ehern. Soc., 1976, 98, 6634.
J.F. Carson, J. ehern. Soc., Perkin Trans. 1, 1977, 1964.
M. Oya, E. Kato, J. Iwao and N. Yasuoka, ehern. Pharrn. Bull., 1982, 30, 484.
18
A
1711
Class 2b
Helralol
A2IJ . 8 .
(R)-(-)
1. (IS,2RH+)1,2epoxy indon • .
2 . (RH+)benzsuberol.
1II
[I)
:So (IS,2 S)-(+)2 - bromo-
CI31
i
[.1)
4. (RH-)2, 2 -dimelhyl"'olrolol.
(RH-);ndon-l'oI
A2IJ.18.
indon -I-ol. A«+l.
IJ. (R)-(+)3,3- dimothylpenlone1,2,5-lnol . Sy AS(H)[/l.
&M. [I~
OH ~[/l
&M. ~ 9 CI~
cO--'OH
CO<
[I]
CI!)
._ ..
?H
?AC
H
cc>--OH
8 . (lS,2RH -)indone-
7. (lR,2RJ-{-)indone-
_____ ~'3:d ~~__ ___ _ ____ _
MOooe~
MIooe)
8. (R)-(-)2,2-dimolhyl- 9. (R)-(-)2-acoloxY'3,3indan- t-ol.
1J 2-diol.
dimethyl91utorie acid
di-Me ut.r.
o={]
10. (SH+)ocloelolhopin .
Abs. X-roy [61
I
11. (RJ-{-)2-hydroxy-3,3-dimelhylsuccinic
oeld di-Mo o,'.r. OA< (- ) T" 41.
- ._ ._ .- .- ._ ._ .__ ._ ._ ." _ . .L ._ ._ ._ ._ .-
A.t"
U ",ö
~
[")
~O--lPh ----w-
:~"
V"b
I
12 .0R,2RH-)l-phenyli 1:S. (1R,2SH+)I'phonyl2-(l-oxopentomelhylene) '
2-(I-oxoponlamolhylene)
oxiran .'Sy AS(H)ol
! oxiran . By AS (H)of
I
(R)-(-)ponloloclono
A':S. 12 .
- ' - ' - T ' _ ._ ._ ._ .- ._ ._ ._ ._ .__ .- ._ ._ .-
(SH-)llovanone
- - ._ .-
(Y'
v.--.O~Ph
14. (5 H-) Ilovon .
A'9.18.
.
1. M. Briancourt, J.P. Guette and A. Horeau, CR. Hebd. Seances Aead. Sei., (e), 1972, 274, 1203, and refs therein.
2. K. Kabuto, M. Imuta, E.S. Kempner and H. Ziffer, J. Org. ehern., 1978,43,2357.
3. M. Imuta and H. Ziffer, J. Org. ehern., 1978, 43, 4540.
4. E .J. Coreyand R.B. Mitra, J. Am. ehern. Soe., 1962, 84, 2938.
5. I. Muzart and J.P. Pete, Tetrahedron Lett., 1977, 303.
6. 'A. Jaunin, Tl. Peteher and H.P. Weber, J. ehern. Soe., Perkin Trans . 2, 1977, 186.
19
