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Enantioselective Brønsted Acid Catalyzed Transfer Hydrogenation: Organocatalytic Reduction of Imines

Organic Letters · 2005 · Vol. 7(17) · pp. 3781–3783

Magnus Rueping✉(Goethe University Frankfurt)Erli Sugiono(Goethe University Frankfurt)Cengiz Azap(Goethe University Frankfurt)Thomas Theissmann(Goethe University Frankfurt)Michael Bolte(Goethe University Frankfurt)

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Abstract

The first enantioselective Brønsted acid catalyzed reduction of imines has been developed. This new organocatalytic transfer hydrogenation of ketimines with Hantzsch dihydropyridine as the hydrogen source offers a mild method to various chiral amines with high enantioselectivity. The stereochemistry of the chiral amines can be rationalized by a stereochemical model derived from an X-ray crystal structure of a chiral BINOL phosphate catalyst. [reaction: see text]

Asymmetric Hydrogenation and Catalysis Asymmetric Synthesis and Catalysis Surface Chemistry and CatalysisEnantioselective synthesisChemistryTransfer hydrogenationBrønsted–Lowry acid–base theoryCatalysisOrganocatalysisCombinatorial chemistryDihydropyridineOrganic chemistry

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Asymmetrische Katalyse durch chirale Wasserstoffbrückendonoren