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Angew Chem Int Ed Engl

Title:		Diastereodivergent synthesis of trisubstituted alkenes through protodeboronation of allylic boronic esters: application to the synthesis of the Californian red scale beetle pheromone
Author(s):		Hesse MJ; Butts CP; Willis CL; Aggarwal VK;
Address:		"School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK"
Journal Title:		Angew Chem Int Ed Engl
Year:		2012
Volume:		20121105
Issue:		50
Page Number:		12444 - 12448
DOI:		10.1002/anie.201207312
ISSN/ISBN:		1521-3773 (Electronic) 1433-7851 (Linking)
Abstract:		E-allylic boronic esters undergo a highly diastereoselective protodeboronation with TBAF?na3 H(2)O to give Z-trisubstituted alkenes. The selectivity can be switched to give predominantly the E-alkene instead by using KHF(2)/TsOH (see scheme). The utility of the methodology has been illustrated in a short synthesis of a component of the sex pheromone of the Californian red scale beetle
Keywords:		Alkenes/chemical synthesis/*chemistry Animals Benzenesulfonates/chemistry Biological Products/chemistry/metabolism Boron/*chemistry Catalysis Coleoptera/metabolism Copper/chemistry Esters Hydrofluoric Acid/chemistry Light Potassium Compounds/chemistry Sex;
Notes:		"MedlineHesse, Matthew J Butts, Craig P Willis, Christine L Aggarwal, Varinder K eng Research Support, Non-U.S. Gov't Germany 2012/11/07 Angew Chem Int Ed Engl. 2012 Dec 7; 51(50):12444-8. doi: 10.1002/anie.201207312. Epub 2012 Nov 5"