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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, Email: kajchem.au.dk

N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Gogevig, K. A. Jorgensen, J. Am. Chem. Soc., 2002, 124, 6254-6255.

DOI: 10.1021/ja026412k (free Supporting Information)


Abstract

L-Proline-catalyzed asymmetric α-amination of ketones proceeds with various azodicarboxylates as the nitrogen source in high yields and excellent enantioselectivities. 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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Key Words

Organocatalysis, α-Amination


ID: J48-Y2002-1130