A new method for the preparation of silyl enol ethers from carbonyl compounds and (Trimethylsilyl)diazomethane in a regiospecific and highly stereoselective manner

被引：60
作者：
Aggarwal, VK
Sheldon, CG
Macdonald, GJ
Martin, WP
机构：
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[2] GlaxoSmithKline, Harlow CN19 5AW, Essex, England
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 35期
关键词：
D O I：
10.1021/ja027061c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The reaction of lithium (trimethylsilyl)diazomethane with aldehydes and ketones has been investigated, and it has been found that quenching at low temperature with MeOH followed by addition of Rh2(OAc)4 gave silyl enol ethers in high yields. Quenching with other electrophiles (e.g., deuterium, MeI) gave terminal and substituted silyl enol ethers with complete control over regio- and stereochemistry. The mechanism of this novel process has been mapped out through a combination of deuterium labeling, ReactIR, and isolation of reaction intermediates. Copyright © 2002 American Chemical Society.
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页码：10300 / 10301
页数：2
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