Synthesis 2013; 45(4): 463-470
DOI: 10.1055/s-0032-1317984
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Cyclic α-Aminophosphonates through Copper-Catalyzed Enamine Activation

Junbin Han
a   Department of Chemistry, University of Louisville, Louisville, KY 40292, USA   Email: bo.xu@louisville.edu   Email: gb.hammond@louisville.edu
,
Robert S. Paton
b   Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK
,
Bo Xu*
a   Department of Chemistry, University of Louisville, Louisville, KY 40292, USA   Email: bo.xu@louisville.edu   Email: gb.hammond@louisville.edu
,
Gerald B. Hammond*
a   Department of Chemistry, University of Louisville, Louisville, KY 40292, USA   Email: bo.xu@louisville.edu   Email: gb.hammond@louisville.edu
› Author Affiliations
Further Information

Publication History

Received: 17 October 2012

Accepted after revision: 12 December 2012

Publication Date:
17 January 2013 (online)


Abstract

A copper-catalyzed tandem-cyclization-triggered addition strategy that relies on electrophilic enamine activation has been used to synthesize various cyclic α-aminophosphonate derivatives in good to excellent yields. Both five- and six-membered rings can be generated under mild conditions with high regioselectivity. A mechanism based on copper-catalyzed enamine activation is proposed.

Supporting Information