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Synfacts 2007(9): 0991-0991  
DOI: 10.1055/s-2007-968875
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Asymmetric Transfer Hydrogenation of β,β-Disubstituted Nitroolefins

Contributor(s): Benjamin List, Kristina Zumbansen
N. J. A. Martin, L. Ozores, B. List*
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
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Publikationsdatum:
23. August 2007 (online)

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Significance

The first organocatalytic enantio­selective transfer hydrogenation of nitroolefins using a Jacobsen-type thiourea catalyst is reported. A broad substrate scope of this reaction is shown. With 5-10 mol% of catalyst good yields (82% to >99%) and high enantioselectivities (er: up to 98:2) are obtained. Aliphatic, aromatic, and sterically hindered substituents R1 in β-position are well tolerated.