Tetrahedron

An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent

G Pinna, MC Bellucci, L Malpezzi, L Pisani, S Superchi…

Index: Pinna, Giovanni; Bellucci, Maria Cristina; Malpezzi, Luciana; Pisani, Laura; Superchi, Stefano; Volonterio, Alessandro; Zanda, Matteo Tetrahedron, 2011 , vol. 67, # 29 p. 5268 - 5281

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Citation Number: 5

Abstract

Abstract N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for α-hydroxy, α-chloro, and α-acetammido benzyl carbanions by means of a two- step sequence involving highly diastereoselective α-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 non-oxidative Pummerer conditions. The ...

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