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Org Lett

Title:		The preparation of nonracemic secondary alpha-(carbamoyloxy)alkylzinc and copper reagents. A versatile approach to enantioenriched alcohols
Author(s):		Papillon JP; Taylor RJ;
Address:		"Department of Chemistry, University of York, Heslington, York YO10 5DD, UK"
Journal Title:		Org Lett
Year:		2002
Volume:		4
Issue:		1
Page Number:		119 - 122
DOI:		10.1021/ol016986e
ISSN/ISBN:		1523-7060 (Print) 1523-7052 (Linking)
Abstract:		"[reaction: see text] Chiral alpha-(carbamoyloxy)alkyllithium reagents, prepared using Hoppe's sBuLi/(-)-sparteine methodology, were transmetalated with ZnCl(2). 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"
Keywords:		4-Butyrolactone/*analogs & derivatives/chemical synthesis Alcohols/*chemical synthesis Animals Carbamates Catalysis Coleoptera *Copper Indicators and Reagents *Organometallic Compounds Sex Attractants/chemical synthesis Stereoisomerism *Zinc;
Notes:		"MedlinePapillon, Julien P N Taylor, Richard J K eng Research Support, Non-U.S. Gov't 2002/01/05 Org Lett. 2002 Jan 10; 4(1):119-22. doi: 10.1021/ol016986e"