Organoboron-Catalyzed Regio- and Stereoselective Formation of β-2-Deoxyglycosidic Linkages

被引：70

作者：

Beale, Thomas M. ^{[1
]}

Moon, Patrick J. ^{[1
]}

Taylor, Mark S. ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 13期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

REGIOSELECTIVE ACTIVATION; DIRECT CONSTRUCTION; GLYCOSIDE FORMATION; GROUP MIGRATION; GLYCOSYLATION; 2-DEOXY-BETA-GLYCOSIDES; DONORS; 2-DEOXY; DIGITOXIN; ACID;

D O I：

10.1021/ol501711v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A borinic acid derived catalyst enables regioselective and beta-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a beta-selective pathway by enhancement of acceptor nucleophilicity constitutes a distinct approach from previous work, which has been aimed at modulating donor reactivity by variation of protective and/or leaving groups.

引用

页码：3604 / 3607

页数：4

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