Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Sciences and Engineering (PSE) Division
Permanent link to this recordhttp://hdl.handle.net/10754/561777
MetadataShow full item record
AbstractA 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.
SponsorsWe 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).
PublisherAmerican Chemical Society (ACS)
- Molecular assembly of an achiral phosphine and a chiral primary amine: a highly efficient supramolecular catalyst for the enantioselective Michael reaction of aldehydes with maleimides.
- Authors: Yang W, Jiang KZ, Lu X, Yang HM, Li L, Lu Y, Xu LW
- Issue date: 2013 Jun
- Primary amine/(+)-CSA salt-promoted organocatalytic conjugate addition of nitro esters to enones.
- Authors: Liu C, Lu Y
- Issue date: 2010 May 21
- Cinchona alkaloid-lewis acid catalyst systems for enantioselective ketene-aldehyde cycloadditions.
- Authors: Zhu C, Shen X, Nelson SG
- Issue date: 2004 May 5
- Asymmetric synthesis of chiral aldehydes by conjugate additions with bifunctional organocatalysis by cinchona alkaloids.
- Authors: Wu F, Hong R, Khan J, Liu X, Deng L
- Issue date: 2006 Jun 26
- Enantioselective organocatalytic alpha-fluorination of aldehydes.
- Authors: Beeson TD, Macmillan DW
- Issue date: 2005 Jun 22