An umpolung sulfoxide reagent as α-hydroxy and α-chloro benzyl carbanion equivalents
A Volonterio, P Bravo, M Zanda
Index: Volonterio, Alessandro; Bravo, Pierfrancesco; Zanda, Matteo Tetrahedron Letters, 2002 , vol. 43, # 37 p. 6537 - 6540
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Abstract
ortho-[(N-Methyl) carbamoyl] phenyl benzyl sulfoxide is used as a synthetic equivalent of α- hydroxy and α-chloro benzyl carbanions by means of a two-step sequence involving (1) highly stereoselective α-C-alkylation with alkyl bromides, and (2) displacement of the sulfinyl group by an OH or a Cl under Pummerer or chloro-Pummerer conditions, respectively. The sulfinyl auxiliary can be effectively regenerated and recycled.
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