Changing course with an additive: A striking example of the effect of TMSCL on lithium amide reactivity

被引：3

作者：

Harrowven, DC

Poon, HS

机构：

[1] Department of Chemistry, University of Southampton, Highfield, Southampton

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 24期

关键词：

D O I：

10.1016/0040-4039(96)00817-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

When a solution of diethyl maleate and acetophenone is added to a cooled (-78 degrees C) solution of a lithium amide the maleate derivative 3 is given in good yield. Pre-treatment of the lithium amide with TMSCl alters the course of this reaction dramatically. With half an equivalent of this additive the Michael adduct 4 is given in 62% yield while employing three equivalents leads to the silyl enol ether 5 in >85% yield. Copyright (C) 1996 Elsevier Science Ltd

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页码：4281 / 4282

页数：2

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