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Direct Organocatalytic Asymmetric α-Chlorination of Aldehydes

Nis Halland, Alan Braunton, Stephan Bachmann, Mauro Marigo and Karl Anker Jørgensen*

*Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark, Email: kajchem.au.dk

N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jorgensen, J. Am. Chem. Soc., 2004, 126, 4790-4791.

DOI: 10.1021/ja049231m (free Supporting Information)


Abstract

A direct organocatalytic enantioselective α-chlorination of aldehydes proceeds for a series of different aldehydes with NCS as the chlorine source using easily available catalysts such as L-proline amide and (2R,5R)-diphenylpyrrolidine. The α-chloro aldehydes are obtained in very good yield and high enantioselectivity.

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Key Words

α-Chlorination, Organocatalysis, N-Chlorosuccinimide (NCS)


ID: J48-Y2004-1470