Issue 91, 2012

Ambiphilic molecules for trapping reactive intermediates: interrupted Nazarov reaction of allenyl vinyl ketones with Me2PCH2AlMe2

Abstract

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.

Graphical abstract: Ambiphilic molecules for trapping reactive intermediates: interrupted Nazarov reaction of allenyl vinyl ketones with Me2PCH2AlMe2

Supplementary files

Article information

Article type
Communication
Submitted
20 Jul 2012
Accepted
28 Sep 2012
First published
28 Sep 2012

Chem. Commun., 2012,48, 11250-11252

Ambiphilic molecules for trapping reactive intermediates: interrupted Nazarov reaction of allenyl vinyl ketones with Me2PCH2AlMe2

J. Boudreau, M. Courtemanche, V. M. Marx, D. Jean Burnell and F. Fontaine, Chem. Commun., 2012, 48, 11250 DOI: 10.1039/C2CC35257E

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