Issue 48, 2012

Chiral sulfoxides in the enantioselective allylation of aldehydes with allyltrichlorosilane: a kinetic study

Abstract

The mechanism of the allylation of aldehydes in the presence of allyltrichlorosilane employing the commercially available (R)-methyl p-tolyl sulfoxide as a Lewis base has been investigated. The combination of kinetic measurements, conductivity analysis and quantum chemical calculations indicates that the reaction proceeds through a dissociative pathway in which an octahedral cationic complex with two sulfoxides is involved. The lack of turnover is ascribed to the formation of neutral sulfurane derivatives.

Graphical abstract: Chiral sulfoxides in the enantioselective allylation of aldehydes with allyltrichlorosilane: a kinetic study

Supplementary files

Article information

Article type
Paper
Submitted
01 Mar 2012
Accepted
22 Oct 2012
First published
22 Oct 2012

Org. Biomol. Chem., 2012,10, 9650-9659

Chiral sulfoxides in the enantioselective allylation of aldehydes with allyltrichlorosilane: a kinetic study

G. Monaco, C. Vignes, F. De Piano, A. Bosco and A. Massa, Org. Biomol. Chem., 2012, 10, 9650 DOI: 10.1039/C2OB27022F

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