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Published January 11, 2006 | Supplemental Material
Journal Article Open

Enantioselective Organocatalytic Reductive Amination


The first enantioselective organocatalytic reductive amination reaction has been accomplished. The development of a new chiral phosphoric acid catalyst has provided a convenient strategy for the enantioselective construction of protected primary amines and provided a highly stereoselective method for the reductive amination of heterocyclic amines. A diverse spectrum of ketone and amine substrates can be accommodated in high yield and excellent enantioselectivity. This new protocol realizes a key benefit of reductive amination versus imine reduction, in that ketimines derived from alkyl−alkyl ketones are unstable to isolation, a fundamental limitation that is comprehensively bypassed using this direct organocatalytic reductive amination.

Additional Information

© 2006 American Chemical Society. Received October 23, 2005. Publication Date (Web): December 14, 2005. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Amgen and Merck. This research was supported by a Marie Curie International Fellowship (to R.I.S.) within the 6th European Community Framework Programme. Joe Carpenter is thanked for catalyst preparation.

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