A one-pot silyl-Reformatsky olefination

James M. Smith, Michael F. Greaney, David Dryden

Research output: Contribution to journalArticlepeer-review

Abstract

A novel one-pot olefination reaction has been developed, involving the stereoselective formation of (E)-alpha,beta-unsaturated esters/ketones from the reaction of alpha-bromocarbonyl compounds with aromatic aldehydes. The reactions use a reagent combination of trichlorosilane, and triethylamine and may proceed via the in situ formation of a trichlorosilyl ketene acetal. The general procedure offers key advantages (high conversions, low quantities of organic soluble by-products) over the conventional Wittig reaction. (C) 2007 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)8687-8690
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number49
DOIs
Publication statusPublished - 3 Dec 2007

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