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Département de Chimie and Centre de Recherche sur la Catalyse et les Interfaces (CERPIC), Université Laval, 1045 Avenue de la Médecine, Québec, Québec, Canada
; Fax: +1 418-656-7916
; Tel: +1 418-656-5140
Department of Chemistry, Dalhousie University, P. O. Box 15000, Halifax, Nova Scotia, Canada
Chem. Commun., 2012,48, 11250-11252
20 Jul 2012,
28 Sep 2012
First published online
28 Sep 2012
The addition of the ambiphilic molecule Me2AlCH2PMe2 (1) to the allenyl vinyl ketone 2 gave a trapped Nazarov reaction product. Under kinetic control, the addition of the phosphine was on the methylated carbon, contrary to expected steric and electronic considerations. Computational data pointed to hydrogen bonding between the phosphine and the methyl group guiding the regiochemistry of this reaction. This product rearranged to provide the expected, regioisomeric Nazarov product. With additional 1 this compound yielded a Michael-addition product via a retro-Nazarov process.
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