Boron aldol additions with erythrulose derivatives:: dependence of stereoselectivity on the type of protecting group

被引：13

作者：

Carda, M ^{[1
]}

Falomir, E

Murga, J

Castillo, E

González, F

Marco, JA

机构：

[1] Univ Jaume 1, Dept Quim Inorgan & Organ, E-12080 Castellon, Spain

[2] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 37期

关键词：

D O I：

10.1016/S0040-4039(99)01380-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Boron aldol additions of 1-O-silylated 3,4-di-O-benzyl- and 3,4-di-O-benzoyl-L-erythrulose and achiral aldehydes using dicyclohexylboron chloride have been investigated. The dibenzyl derivative gave syn/syn stereoisomers with high stereoselectivity, whereas the dibenzoyl derivative gave syn/anti stereoisomers. It is believed that, while the dibenzoyl erythrulose gives rise to the E enolate in the presence of dicyclohexylboron chloride, as usually observed with this reagent, only the Z enolate is formed in the case of the dibenzyl derivative. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：6845 / 6848

页数：4

共 33 条

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