Synfacts 2006(4): 0390-0390  
DOI: 10.1055/s-2006-932101
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Thiourea-Catalyzed Reductive Amination of Ketones

Contributor(s): Benjamin List, Nolwenn J. A. Martin
D. Menche*, J. Hassfeld, J. Li, G. Menche, A. Ritter, S. Rudolph
Gesellschaft für Biotechnologische Forschung mbH, Braunschweig, Germany
Further Information

Publication History

Publication Date:
24 March 2006 (online)

Significance

An efficient, non-asymmetric, organocatalytic, direct reductive amination of ketones is described. This reaction proceeds under mild and acid-free conditions and is catalyzed by commercially available thiourea 1. It is assumed to proceed via activation of the in situ generated ketimine through hydrogen bonding interactions with thiourea 1 followed by reduction with commercially available Hantzsch ester 2. The reaction works well with a wide range of ketones in combination with aryl or heteroaromatic primary amines providing the corresponding secondary amines in moderate to excellent yields within 48 hours.