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Enantioselective Protonation Catalyzed by a Chiral Bicyclic Guanidine Derivative
Author(s) -
Leow Dasheng,
Lin Shishi,
Chittimalla Santhosh Kumar,
Fu Xiao,
Tan ChoonHong
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200801378
Subject(s) - enantioselective synthesis , protonation , chemistry , guanidine , conjugate , derivative (finance) , catalysis , aryl , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , ion , mathematical analysis , alkyl , mathematics , financial economics , economics
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; R 1 –R 4 =H, Me, Cl, F.