α-Amination of Phosphonates: A Direct Synthesis of α-Amino Phosphonic Acids and Their Derivatives

Stacey L. McDonald; Qiu Wang

doi:10.1055/s-0034-1378324

Synlett, Table of Contents

Synlett 2014; 25(16): 2233-2238
DOI: 10.1055/s-0034-1378324

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α-Amination of Phosphonates: A Direct Synthesis of α-Amino Phosphonic Acids and Their Derivatives

Stacey L. McDonald

Department of Chemistry, Duke University, Durham, NC 27708–0346, USA Email: qiu.wang@duke.edu

,

Qiu Wang*

Department of Chemistry, Duke University, Durham, NC 27708–0346, USA Email: qiu.wang@duke.edu

› Author Affiliations

Abstract

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Abstract

A direct approach to access important α-amino phosphonic acids and their derivatives through the formation of C–N bonds is described. Several α-amination reactions of phosphonates that involve electrophilic aminating agents are reviewed. A recent development is highlighted in which an acyclic or cyclic amine is introduced into the α-position of a phosphonate in one step through deprotonative formation of an α-zincate followed by copper-catalyzed amination with an O-acylhydroxylamine.

Key words

aminophosphonic acids - amination - phosphonates - copper catalysis - O-acylhydroxylamines - C–N bond formation

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References

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