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 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.

An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent / G. Pinna, M. C. Bellucci, L. Malpezzi, L. Pisani, S. Superchi, A. Volonterio, M. Zanda. - In: TETRAHEDRON. - ISSN 0040-4020. - 67:29(2011), pp. 5268-5281.

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

M. C. Bellucci
Secondo
;
2011

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 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.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/171286
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