Extremely efficient chiral induction in conjugate additions of p-tolyl α-lithio-β-(trimethylsilyl)ethyl sulfoxide and subsequent electrophilic trapping reactions

被引：40

作者：

Nakamura, S ^{[1
]}

Watanabe, Y ^{[1
]}

Toru, T ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 06期

关键词：

D O I：

10.1021/jo991635n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of p-tolyl alpha-lithio-beta-(trimethylsilyl)ethyl sulfoxide with alpha,beta-unsaturated esters gave the conjugate addition products as a single diastereomer. The intermediate enolates were subsequently trapped with various alkyl halides or aldehydes to give the products with extremely high stereoselectivity. The reaction with alpha,beta-unsaturated ketones also proceeded with high diastereo-selectivity. Protolysis of the enolates derived from the alpha-methyl-alpha,beta-unsaturated esters gave the products with high stereoselectivity. The stereo- and regioselective elimination of the sulfinyl group gave chiral homoallylic carboxylates.

引用

页码：1758 / 1766

页数：9

共 55 条

[51] ASYMMETRIC CARBON-CARBON BOND FORMATION USING SULFOXIDE-STABILIZED CARBANIONS [J].