Direct l-Proline-Catalyzed Asymmetric α-Amination of Ketones

Nagaswamy Kumaragurubaran, Karsten Juhl, Wei Zhuang, Anders Bøgevig, and Karl Anker Jørgensen*
Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark
J. Am. Chem. Soc., 2002, 124 (22), pp 6254–6255
DOI: 10.1021/ja026412k
Publication Date (Web): May 11, 2002
Copyright © 2002 American Chemical Society
*

 To whom correspondence should be addressed. Fax:  45 8619 6199. Telephone:  45 8942 3910. E-mail:  kaj@chem.au.dk.

Abstract

Abstract Image

The first direct catalytic asymmetric α-amination of ketones catalyzed by l-proline has been developed. The reactions proceed with various azodicarboxylates as the nitrogen source in high yields and excellent enantioselectivities (up to 99% ee). The scope and potential of the reaction are demonstrated by further transformation of the α-hydrazino ketones formed to both optically active syn and anti-α-amino alcohol derivatives.

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History

  • Published In Issue June 05, 2002
  • Received April 4, 2002

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