Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins

Jakob F. Schneider; Markus B. Lauber; Vanessa Muhr; Domenic Kratzer; Jan Paradies

doi:10.1039/C1OB05059A

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Organic & Biomolecular Chemistry

Issue 11, 2011

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Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins

Jakob F. Schneider , Markus B. Lauber , Vanessa Muhr , Domenic Kratzer and Jan Paradies

Org. Biomol. Chem., 2011,9, 4323-4327

DOI: 10.1039/C1OB05059A
Received 11 Jan 2011, Accepted 14 Mar 2011
First published on the web 14 Apr 2011

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Abstract
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This paper focuses on readily accessible thiourea hydrogen bond catalysts derived from amino acids, whose steric and electronic features are modulated by their degree of substitution at the carbinol carbon center. These catalysts were applied in the asymmetric transfer hydrogenation of nitroolefins furnishing the chiral products in up to 99% yield and 86% enantiomeric excess. The proposed catalyst's mode of action is supported by mechanistic investigations.