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Synfacts 2010(1): 0100-0100  
DOI: 10.1055/s-0029-1218494
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

A New Approach to Asymmetric DMAP Catalysis

Contributor(s): Benjamin List, Olga Lifchits
C. K. De, E. G. Klauber, D. Seidel*
Rutgers, The State University of New Jersey, Piscataway, USA
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

Seidel and colleagues report the ­kinetic resolution of benzylic amines using DMAP in combination with catalytic thiourea 1 and benzoic anhydride 2 as the acylating agent. The novelty of this approach lies in the use of an achiral Lewis base catalyst which forms an ion pair with the acylating agent (complex I). This complex is made reactive and chiral when the thiourea co-catalyst binds the anion through hydrogen-bonding interactions (complex II).