Metal-mediated, completely diastereofacial conjugate addition of trialkylstannylmetal reagents to γ-alkoxy-α,β-unsaturated esters

A. Krief, L. Provins, W. Dumont

Research output: Contribution to journalArticle

Abstract

Complete control of the face of attack in the addition of stannylmetal reagents to γ-alkoxy-α,β-unsaturated esters can be achieved by using the appropriate counterion (see scheme). The stereochemistry of addition does not depend on the configuration of the C-C double bond, although the stereoselectivity is consistently better with the Z stereoisomer, for which 100% Si attack is obtained with Li as counterion and 100% Re attack with LiZnEt.
Original languageEnglish
Pages (from-to)1946-1948
Number of pages3
JournalAngewandte Chemie. International edition
Volume38
Issue number13-14
Publication statusPublished - 12 Jul 1999

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