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Synfacts 2009(11): 1284-1284  
DOI: 10.1055/s-0029-1218109
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Hydrogen-Bond-Assisted Hydrogen-Bonding Catalysis

Contributor(s): Benjamin List, Frank Lay
C. R. Jones, G. D. Panto , A. J. Morrison, M. D. Smith*
University of Oxford, University of Cambridge and Schering Plough Corporation, Newhouse, UK
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

Smith and co-workers designed a new type of hydrogen-bonding thiourea catalyst 1 mimicking the positively cooperative action of enzymes. The improvement of asymmetric induction and the significantly increased catalytic efficiency compared to thiourea catalyst 2 that does not bear an additional hydrogen-bond-donor group are demonstrated in a Mukaiyama-Mannich reaction, by catalyst competition experiments, and by measuring the anion-binding ability.