Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis
Type
ArticleKAUST Department
Biological and Environmental Sciences and Engineering (BESE) DivisionChemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2011-05-20Permanent link to this record
http://hdl.handle.net/10754/561777
Metadata
Show full item recordAbstract
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/ol200747xSponsors
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 LettersPubMed ID
21510614ae974a485f413a2113503eed53cd6c53
10.1021/ol200747x
Scopus Count
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