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Enantioselective Organocatalytic Reductive Amination

Storer, R. Ian and Carrera, Diane E. and Ni, Yike and MacMillan, David W. C. (2006) Enantioselective Organocatalytic Reductive Amination. Journal of the American Chemical Society, 128 (1). pp. 84-86. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170421-110406223

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Abstract

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.


Item Type:Article
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http://dx.doi.org/10.1021/ja057222nDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja057222nPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja057222nPublisherSupporting Information
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.
Funders:
Funding AgencyGrant Number
NIHR01 GM66142-01
AmgenUNSPECIFIED
MerckUNSPECIFIED
Marie Curie FellowshipUNSPECIFIED
Issue or Number:1
Record Number:CaltechAUTHORS:20170421-110406223
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170421-110406223
Official Citation:Enantioselective Organocatalytic Reductive Amination R. Ian Storer, Diane E. Carrera, Yike Ni, and David W. C. MacMillan Journal of the American Chemical Society 2006 128 (1), 84-86 DOI: 10.1021/ja057222n
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76817
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:21 Apr 2017 20:28
Last Modified:03 Oct 2019 17:50

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