Understanding the π-facial diastereoselectivity in the addition of chiral diaminophosphino(silyl)carbenes to activated olefins

Ona Illa, Xavier Bagan, Antoine Baceiredo, Vicenç Branchadell, Rosa M. Ortuño

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5 Citations (Scopus)

Abstract

The synthesis of a new chiral diaminophosphino(silyl)carbene, based on the use of (R,R)-cyclohexane-trans-1,2-diamine, is described. Its reaction with methyl acrylate afforded a cyclopropane derivative as a single diastereomer. The diastereoselectivity in the addition reactions between olefins and chiral carbenes derived from C2-symmetric diamines has also been studied by theoretical calculations, which establish that it has a steric origin; we report a rationale to predict the absolute configuration of the adducts. © 2008 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)2353-2358
JournalTetrahedron Asymmetry
Volume19
Issue number20
DOIs
Publication statusPublished - 20 Oct 2008

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