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Title: Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis
Authors: Liu, C.
Zhu, Q.
Huang, K.-W.
Lu, Y. 
Issue Date: 20-May-2011
Citation: Liu, C.,Zhu, Q.,Huang, K.-W.,Lu, Y. (2011-05-20). Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis. Organic Letters 13 (10) : 2638-2641. ScholarBank@NUS Repository.
Abstract: A novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (-)-CSA was found to be the best catalyst with matching chirality, enabling the direct amination of α-branched aldehydes to proceed in quantitative yields and with nearly perfect enantioselectivities. A 0.5 mol % catalyst loading was sufficient to catalyze the reaction, and a gram scale enantioselective synthesis of biologically important α-methyl phenylglycine has been successfully demonstrated. © 2011 American Chemical Society.
Source Title: Organic Letters
ISSN: 15237060
DOI: 10.1021/ol200747x
Appears in Collections:Staff Publications

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