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Synthesis 2009(24): 4125-4128  
DOI: 10.1055/s-0029-1217070
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

N-Heterocyclic Carbene Catalyzed Nucleophilic Acylation of Trifluoromethyl Ketimines

Dieter Enders*, Alexander Henseler, Sebastian Lowins
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(214)8092127; e-Mail: enders@rwth-aachen.de;
Further Information

Publication History

Received 28 August 2009
Publication Date:
22 October 2009 (online)

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Abstract

An efficient N-heterocyclic carbene (NHC)-catalyzed nucleophilic acylation of trifluoromethyl ketimines has been developed. The combination of N-aryl trifluoromethyl ketimines with various furan-2-carbaldehydes leads chemoselectively to the corresponding α-amino-α-trifluoromethyl ketones in moderate to very good yields (32-87%) providing ready access to this pharmaceutically important class of compounds.

Key words

organocatalysis - N-heterocyclic carbenes - aldehyde/ketimine cross-coupling - α-amino-α-trifluoromethyl ketones - umpolung

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