An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion

Matteo Zanda, Giovanni Pinna

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for a-hydroxy, a-chloro, and a-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective a-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under nonoxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the reaction, as well as the mechanism of the process are discussed in detail.
Original languageEnglish
Pages (from-to)5268-5281
Number of pages14
JournalTetrahedron
Volume67
Issue number29
DOIs
Publication statusPublished - 22 Jul 2011

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