CARBOHYDRATES AS CHIRAL AUXILIARIES - THE ASYMMETRIC EPOXIDATION REACTION OF OLEFINS

被引：18

作者：

CHARETTE, AB

COTE, B

机构：

[1] Département de chimie, Université de Montréal, Montréal

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(00)80083-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Under optimized conditions, the epoxidation of 1-O-trans-2-butenyl-3,4,6-tri-O-benzyl-beta-D-glucopyranose gave a 9:1 mixture of diastereomers. The diastereoselectivities observed were shown to be highly dependent on the nature of the reagent used and of the protecting group at C-2 of the auxiliary.

引用

页码：2283 / 2286

页数：4

共 21 条

[1] BOYD MR, 1989, J NATL CANCER I, V81, P1254
[2] EPOXIDATION OF ALLYLIC ALCOHOLS WITH PEROXY-ACIDS - ATTEMPTS TO DEFINE TRANSITION STATE GEOMETRY
CHAMBERL.P
ROBERTS, ML
WHITHAM, GH
[J]. JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (07): : 1374 - &
[3] CARBOHYDRATES AS CHIRAL AUXILIARIES - ASYMMETRIC CYCLOPROPANATION REACTION OF ACYCLIC OLEFINS
CHARETTE, AB
COTE, B
MARCOUX, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) : 8166 - 8167
[4] TOTAL SYNTHESIS OF VENUSTATRIOL
COREY, EJ
HA, DC
[J]. TETRAHEDRON LETTERS, 1988, 29 (26) : 3171 - 3174
[5] 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
[6] THE SYNTHETIC METHODOLOGY OF NONRACEMIC GLYCIDOL AND RELATED 2,3-EPOXY ALCOHOLS
HANSON, RM
[J]. CHEMICAL REVIEWS, 1991, 91 (04) : 437 - 475
[7] HENBEST HB, 1963, P CHEM SOC LONDON, P159
[8] SUBSTRATE-DIRECTABLE CHEMICAL-REACTIONS
HOVEYDA, AH
EVANS, DA
FU, GC
[J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1307 - 1370
[9] JORGENSEN KA, 1989, CHEM REV, V89, P431
[10] CARBOHYDRATES AS CHIRAL AUXILIARIES IN STEREOSELECTIVE SYNTHESIS
KUNZ, H
RUCK, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (03) : 336 - 358

← 1 2 3 →