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" |
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" |