Iron-catalyzed Doyle-Kirmse reaction of allyl sulfides with (trimethylsilyl)diazomethane

被引：48

作者：

Carter, DS ^{[1
]}

Van Vranken, DL ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 09期

关键词：

D O I：

10.1021/ol005740r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iron salts efficiently catalyze the Doyle-Kirmse reaction of allyl sulfides with (trimethylsilyl)diazomethane and ethyl diazoacetate in dichloroethane at 83 degrees C. Competitive dimerization is less of a problem with (trimethylsilyl)diazomethane than with ethyl diazoacetate. Good results are obtained using only 1.5 equiv of (trimethylsilyl)diazomethane, even without slow addition. Phosphine ligands affect the kinetics, but not the diastereoselectivity. Dppe and BINAP lead to higher yields than dppp, but no enantioselection was detected with R-(+)-BINAP.

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页码：1303 / 1305

页数：3

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