Letter
The Preparation of Nonracemic Secondary α-(Carbamoyloxy)alkylzinc and Copper Reagents. A Versatile Approach to Enantioenriched Alcohols
In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.
Abstract

Chiral α-(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.
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History
- Published In Issue January 10, 2002
- Received November 1, 2001
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