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J Org Chem


Title:Catalytic enantioselective synthesis of vicinal dialkyl arrays
Author(s):van Zijl AW; Szymanski W; Lopez F; Minnaard AJ; Feringa BL;
Address:"Stratingh Institute for Chemistry, Faculty of Mathematics and Natural Sciences, University of Groningen, Nijenborgh 4, 9747AG, Groningen, The Netherlands"
Journal Title:J Org Chem
Year:2008
Volume:20080807
Issue:18
Page Number:6994 - 7002
DOI: 10.1021/jo8010649
ISSN/ISBN:1520-6904 (Electronic) 0022-3263 (Linking)
Abstract:With a consecutive 'asymmetric allylic alkylation (AAA)/cross-metathesis (CM)/conjugate addition (CA)' protocol it is possible to synthesize either stereoisomer of compounds containing a vicinal dialkyl array with excellent stereoselectivity. The versatility of this protocol in natural product synthesis is demonstrated in the preparation of the ant pheromones faranal and lasiol
Keywords:Alcohols/*chemical synthesis/chemistry Aldehydes/*chemical synthesis/chemistry Alkylation Animals Ants Catalysis Copper/chemistry Esters/*chemical synthesis/chemistry Ketones/*chemical synthesis/chemistry Molecular Conformation Pheromones/*chemical synthe;
Notes:"Medlinevan Zijl, Anthoni W Szymanski, Wiktor Lopez, Ferrnando Minnaard, Adriaan J Feringa, Ben L eng Research Support, Non-U.S. Gov't 2008/08/08 J Org Chem. 2008 Sep 19; 73(18):6994-7002. doi: 10.1021/jo8010649. Epub 2008 Aug 7"

 
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