The Preparation of Nonracemic Secondary α-(Carbamoyloxy)alkylzinc and Copper Reagents. A Versatile Approach to Enantioenriched Alcohols

Julien P. N. Papillon and Richard J. K. Taylor*
Department of Chemistry, University of York, Heslington, York YO10 5DD, U.K.
Org. Lett., 2002, 4 (1), pp 119–122
DOI: 10.1021/ol016986e
Publication Date (Web): December 12, 2001
Copyright © 2002 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, rjkt1@york.ac.uk

Abstract

Abstract Image

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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