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
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
收藏
页码:119 / 122
页数:4
相关论文
共 52 条