ALKENYL OXAZOLIDINONES BY STEREOSELECTIVE EPOXIDATION OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES - SYNTHESIS OF ANY ISOMER (RR, RS, SR OR SS, E OR Z) BEARING 1,4-RELATED CHIRAL CENTERS ACROSS A DOUBLE-BOND

被引：34

作者：

CLAYDEN, J

COLLINGTON, EW

LAMONT, RB

WARREN, S

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND

[2] GLAXO GRP RES LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(00)60383-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkenyl oxazolidinones 5 have been made from the urethane derivatives 4 of diphenylphosphinoyl epoxy alcohols 1 by a tandem intramolecular ring closure - Horner-Wittig elimination sequence. The stereoisomers of diphenylphosphinoyl epoxy alcohols containing further chiral centres have been made by enantio- and diastereoselective epoxidation, and converted stereospecifically to alkenyl oxazolidinones with 1,4-related chiral centres across a controlled geometry double bond.

引用

页码：2203 / 2206

页数：4

共 15 条

[1] TRANSFORMATION OF CYCLIC ALPHA-PHENYLTHIO ALDEHYDES BY STEREOSELECTIVE ALDOL REACTIONS AND PHENYLTHIO MIGRATION INTO SPIROCYCLIC LACTONES AND ETHERS, AND E-ALLYLIC ALCOHOLS WITH 1,4-RELATED CHIRAL CENTERS
AGGARWAL, VK
COLDHAM, I
MCINTYRE, S
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02): : 451 - 460
[2] SYNTHESIS OF CHIRAL VINYLGLYCINES
BEAULIEU, PL
DUCEPPE, JS
JOHNSON, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) : 4196 - 4204
[3] THE STEREOCONTROLLED HORNER-WITTIG REACTION - SYNTHESIS OF DISUBSTITUTED ALKENES
BUSS, AD
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2307 - 2325
[4] ASYMMETRIC EPOXIDATIONS AND KINETIC RESOLUTIONS OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES
CLAYDEN, J
COLLINGTON, EW
WARREN, S
[J]. TETRAHEDRON LETTERS, 1992, 33 (46) : 7043 - 7046
[5] STEREOCONTROLLED SYNTHESIS OF R OR S, E OR Z UNSATURATED ALPHA-AMINO-ACIDS BY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE EPOXIDATION OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES
CLAYDEN, J
COLLINGTON, EW
WARREN, S
[J]. TETRAHEDRON LETTERS, 1993, 34 (08) : 1327 - 1330
[6] THE SYNTHESIS OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES BY PALLADIUM(II)-CATALYZED ALLYLIC TRANSPOSITION
CLAYDEN, J
COLLINGTON, EW
WARREN, S
[J]. TETRAHEDRON LETTERS, 1992, 33 (46) : 7039 - 7042
[7] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION
GAO, Y
HANSON, RM
KLUNDER, JM
KO, SY
MASAMUNE, H
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) : 5765 - 5780
[8] SYNTHESIS OF Z-ALLYLIC ALCOHOLS WITH 1,4-RELATED CHIRAL CENTERS BY STEREOSELECTIVE EPOXIDATION AND THE HORNER-WITTIG REACTION
HALL, D
SEVIN, AF
WARREN, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (48) : 7123 - 7126
[9] HARTLEY RC, IN PRESS TETRAHEDRON
[10] HIGHLY SELECTIVE SYNTHESIS OF (E)-ALKENE ISOSTERIC DIPEPTIDES WITH HIGH OPTICAL PURITY VIA RCU(CN)LI.BF3 MEDIATED REACTION
IBUKA, T
HABASHITA, H
FUNAKOSHI, S
FUJII, N
OGUCHI, Y
UYEHARA, T
YAMAMOTO, Y
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (07): : 801 - 803

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