Erythrulose as a multifunctional chiron: Highly stereoselective boron aldol additions

被引：17

作者：

Marco, JA ^{[1
]}

Carda, M

Falomir, E

Palomo, C

Oiarbide, M

Ortiz, JA

Linden, A

机构：

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

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

[3] Univ Basque Country, Fac Quim, Dept Quim Organ, E-20080 San Sebastian, Spain

[4] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(99)80113-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have investigated the formation of various metal enolates of 1-O-silylated erythrulose 3,4-acetonides. We were able to prepare boron enolates using Brown's dicyclohexylboron chloride/tertiary amine system. When these enolates were allowed to react with a range of achiral aldehydes, highly stereoselective aldol additions took place with formation of the syn/syn stereoisomer. This has been attributed to the exclusive formation of a Z boron enolate, which is in a sharp contrast with the usual behaviour of the aforementioned reagent. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1065 / 1068

页数：4

共 53 条

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