Please use this identifier to cite or link to this item: https://doi.org/10.1002/anie.200801378
Title: Enantioselective protonation catalyzed by a chiral bicyclic guanidine derivative
Authors: Leow, D.
Lin, S.
Chittimalla, S.K.
Fu, X. 
Tan, C.-H. 
Keywords: Amino acids
Atropisomerism
Deuteration
Enantioselectivity
Protonation
Issue Date: 14-Jul-2008
Citation: Leow, D., Lin, S., Chittimalla, S.K., Fu, X., Tan, C.-H. (2008-07-14). Enantioselective protonation catalyzed by a chiral bicyclic guanidine derivative. Angewandte Chemie - International Edition 47 (30) : 5641-5645. ScholarBank@NUS Repository. https://doi.org/10.1002/anie.200801378
Abstract: (Chemical Equation Presented) Simple is beautiful: The guanidine derivative 1 catalyzes a tandem conjugate addition-enantioselective protonation reaction of phthalimidoacrylates with thiols (see scheme) and itaconimides with phosphine oxides. Optically pure analogues of cysteine and cystine were obtained in this way. In highly enantioselective deuteration reactions, a small but significant kinetic isotope effect was observed. R=aryl, benzhydryl; R1-R 4=H, Me, Cl, F. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
Source Title: Angewandte Chemie - International Edition
URI: http://scholarbank.nus.edu.sg/handle/10635/93741
ISSN: 14337851
DOI: 10.1002/anie.200801378
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