An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion

Matteo Zanda; Giovanni Pinna

doi:10.1016/j.tet.2011.05.033

An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion

Matteo Zanda, Giovanni Pinna

Medical Sciences

Research output: Contribution to journal › Article › peer-review

17 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 language	English
Pages (from-to)	5268-5281
Number of pages	14
Journal	Tetrahedron
Volume	67
Issue number	29
DOIs	https://doi.org/10.1016/j.tet.2011.05.033
Publication status	Published - 22 Jul 2011

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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. ",

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AU - Pinna, Giovanni

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N2 - 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.

AB - 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.

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An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion

Abstract

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