« Previous AbstractMesoporous molecular sieve-based materials for catalytic oxidation of VOC: A review    Next AbstractHeadspace solid-phase microextraction combined with GCxGC-TOFMS for the analysis of volatile compounds of Coptis species rhizomes »

J Am Chem Soc

Title:		3-Boronoacrolein as an exceptional heterodiene in the highly enantio- and diastereoselective Cr(III)-catalyzed three-component [4+2]/allylboration
Author(s):		Gao X; Hall DG;
Address:		"Department of Chemistry, University of Alberta, Edmonton, AB, T6G 2G2, Canada"
Journal Title:		J Am Chem Soc
Year:		2003
Volume:		125
Issue:		31
Page Number:		9308 - 9309
DOI:		10.1021/ja036368o
ISSN/ISBN:		0002-7863 (Print) 0002-7863 (Linking)
Abstract:		"This Communication reports the optimization of the first catalytic enantio- and diastereoselective hetero[4+2]/allylboration reaction to provide efficient access to alpha-hydroxyalkyl pyran derivatives. The key substrate 3-boronoacrolein pinacolate appears to be an exceptionally favorable heterodiene for use in Jacobsen's enantioselective reverse electron demand hetero[4+2] reaction with enol ethers, catalyzed by the tridentate (Schiff base)chromium complex 1. This one-pot three-component reaction was successfully applied to a concise total synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide (2), the oviposition attractant pheromone of the female Culex mosquito capable of transmitting the West Nile virus"
Keywords:		Acrolein/*analogs & derivatives Allyl Compounds/*chemistry Boron Compounds/*chemistry Catalysis Chromium/chemistry Cyclization Pyrans/*chemical synthesis Stereoisomerism;
Notes:		"MedlineGao, Xuri Hall, Dennis G eng Research Support, Non-U.S. Gov't 2003/08/02 J Am Chem Soc. 2003 Aug 6; 125(31):9308-9. doi: 10.1021/ja036368o"