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Synfacts 2006(3): 0279-0279  
DOI: 10.1055/s-2006-931984
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Phosphoric Acid Catalyzed Enantioselective Reductive Amination

Contributor(s): Benjamin List, Nolwenn J. A. Martin
R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan*
California Institute of Technology, Pasadena, USA
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

An efficient and highly enantioselective, organocatalytic reductive amination is described. This reaction proceeds under simple and mild conditions and is catalyzed by phosphoric acid derivative 1. It is assumed to proceed via protonation of the in situ generated ketimine, which undergoes reduction in the presence of commercially available Hantzsch ester 2. The simple fragment coupling works with a wide range of aryl-alkyl or alkyl-alkyl ketones in combination with aryl or heterocyclic amines.