Enantioselective copper-catalyzed cyclopropanation of silyl enol ethers

被引:30
作者
Ebinger, A [1 ]
Heinz, T [1 ]
Umbricht, G [1 ]
Pfaltz, A [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
D O I
10.1016/S0040-4020(98)00499-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper(I) complexes derived from semicorrins, azasemicorrins and bisoxazolines are efficient catalysts for the enantioselective cyclopropanation of silyl enol ethers with diazoacetates. The resulting cyclopropanes can be converted to gamma-ketocarboxylates by acid-induced ring cleavage. In this way methyl (2-oxocyclopentyl)- and (2-oxocyclohexyl)acetates have been prepared with up to 90 and 80% ee, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:10469 / 10480
页数:12
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