Stereoselective enol tosylation:: Preparation of trisubstituted α,β-unsaturated esters

被引：80

作者：

Baxter, JM ^{[1
]}

Steinhuebel, D ^{[1
]}

Palucki, M ^{[1
]}

Davies, IW ^{[1
]}

机构：

[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 02期

关键词：

D O I：

10.1021/ol047854z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective preparation of (E)- or (Z)-trisubstituted alpha,beta-unsaturated esters in three steps from N-protected glycine is presented. The key step in the synthesis is the highly selective enol tosylation of gamma-amino beta-keto esters. The enol tosylates are stable. crystalline compounds that undergo smooth and effective Suzuki-Miyaura coupling reaction with a variety of aryl boronic acids.

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页码：215 / 218

页数：4

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