The preparation of nonracemic secondary α-(carbamoyloxy)alkylzinc and copper reagents.: A versatile approach to enantioenriched alcohols

被引：50

作者：

Papillon, JPN ^{[1
]}

Taylor, RJK ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 01期

关键词：

D O I：

10.1021/ol016986e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS Chiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl2. Further transmetalation with CuCN with overall retention of configuration gave chiral species that reacted with various electrophiles to give enantiomerically pure alcohols after deprotection. A short, highly efficient synthesis of an industrially relevant pheromone, japonilure, illustrates the value of the methodology.

引用

页码：119 / 122

页数：4

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