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    Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis

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    Type
    Article
    Authors
    Liu, Chen
    Zhu, Qiang
    Huang, Kuo-Wei cc
    Lu, Yixin
    KAUST Department
    Biological and Environmental Sciences and Engineering (BESE) Division
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2011-05-20
    Permanent link to this record
    http://hdl.handle.net/10754/561777
    
    Metadata
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    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.
    Citation
    Liu, C., Zhu, Q., Huang, K.-W., & Lu, Y. (2011). Primary Amine/CSA Ion Pair: A Powerful Catalytic System for the Asymmetric Enamine Catalysis. Organic Letters, 13(10), 2638–2641. doi:10.1021/ol200747x
    Sponsors
    We are grateful for the generous financial support from the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112).
    Publisher
    American Chemical Society (ACS)
    Journal
    Organic Letters
    DOI
    10.1021/ol200747x
    PubMed ID
    21510614
    ae974a485f413a2113503eed53cd6c53
    10.1021/ol200747x
    Scopus Count
    Collections
    Articles; Biological and Environmental Sciences and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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