Catalytic enantioselective desymmetrization of COT-monoepoxide.: Maximum deviation from coplanarity for an SN2′-cuprate alkylation

被引：23

作者：

Del Moro, F ^{[1
]}

Crotti, P ^{[1
]}

Di Bussolo, V ^{[1
]}

Macchia, F ^{[1
]}

Pineschi, M ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Biorgan & Biofarm, I-56126 Pisa, Italy

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 11期

关键词：

D O I：

10.1021/ol034554t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] The first alkylative and enantioselective ring-opening of COT-monoepoxide (1) without the occurrence of any ring-contraction-isomerization by the use of in situ-formed organocuprates is reported. Because of the particular geometric constraint of compound 1, this work reports the largest deviation from coplanarity between the pi-orbital of the double bond and the sigma-bond connecting the leaving group ever observed for an S(N)2'-cuprate alkylation.

引用

页码：1971 / 1974

页数：4

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