REVERSAL OF ALDEHYDE DIASTEREOFACIAL SELECTIVITY IN A METHYL KETONE ALDOL REACTION - APPLICATION TO THE SYNTHESIS OF THE CALYCULIN SPIROKETAL

被引：60

作者：

EVANS, DA

GAGE, JR

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 43期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)97005-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It has been observed that aldehyde diastereofacial selectivity in a methyl ketone aldol reaction can be fully regulated under appropriate conditions. Addition of the lithium enolate provided the product derived from apparent chelation control, while Lewis acid-promoted addition of the derived silyl enol ether afforded the Felkin-Anh diastereomer. Application of this methodology to the ongoing synthesis of calysulin A is presented. © 1990.

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页码：6129 / 6132

页数：4

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