Synlett 2014; 25(16): 2233-2238
DOI: 10.1055/s-0034-1378324
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© Georg Thieme Verlag Stuttgart · New York

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
Further Information

Publication History

Received: 02 May 2014

Accepted after revision: 20 May 2014

Publication Date:
07 July 2014 (online)


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.

 
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