Pentanidium-catalyzed enantioselective phase-transfer conjugate addition reactions
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
KAUST Catalysis Center (KCC)
Chemical Science Program
Physical Sciences and Engineering (PSE) Division
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AbstractA new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β- unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications of this methodology. Phosphoglycine ester analogues can also be utilized as the Michael donor, affording enantioenriched α-aminophosphonic acid derivatives and phosphonic analogues of (S)-proline. © 2011 American Chemical Society.
SponsorsThis work was supported by a research grant (R-143-000-342-112) and a scholarship (to M.T.) from NUS.
PublisherAmerican Chemical Society (ACS)
Is Supplemented ByMa, T., Fu, X., Kee, C. W., Zong, L., Pan, Y., Huang, K.-W., & Tan, C.-H. (2011). CCDC 836212: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccx24lp
Ma, T., Fu, X., Kee, C. W., Zong, L., Pan, Y., Huang, K.-W., & Tan, C.-H. (2011). CCDC 836213: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccx24mq