Enantioselective Hydrogenation of Allylphthalimides: An Efficient Method for the Synthesis of [beta]-Methyl Chiral AminesThis work was supported by the National Institutes of Health. We acknowledge the generous gift of Ru complexes from Heraeus Inc.

Abstract

treatment of asthma. Compound B (NPS 1392) is a potent stereoselective antagonist of the NMDA receptor, which can be used for the control of ischemic strokes. To our knowledge, there has been no successful catalytic method to make such important functional groups. Although some stoichiometric asymmetric synthesis or resolution routes have been reported for constructing this class of chiral amines, the development of efficient and catalytic synthetic methods remains a significant challenge. Herein we report the first highly enantioselective catalytic asymmetric hydrogenation of disubstituted allylphthalimides to form chiral phthalimides, which act as precursors to the b-methyl chiral amines [Eq. (1)].

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