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Palladium‐Catalyzed Asymmetric Hydrogenolysis of N ‐Sulfonyl Aminoalcohols via Achiral Enesulfonamide Intermediates
Author(s) -
Yu ChangBin,
Zhou YongGui
Publication year - 2013
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.201307036
Subject(s) - hydrogenolysis , trifluoroacetic acid , chemistry , catalysis , isomerization , sulfonyl , stereocenter , palladium , enamine , imine , organic chemistry , medicinal chemistry , combinatorial chemistry , enantioselective synthesis , alkyl
Giving the cat complete control : A stereoconvergent formal hydrogenolysis of N ‐sulfonyl aminoalcohols in the presence of a chiral Pd catalyst and trifluoroacetic acid (TFA) gave chiral amines with two contiguous stereocenters (see scheme; TFE=trifluoroethanol, Ts= p ‐tosyl). The products were formed with up to 94 % ee by acid‐catalyzed dehydration to afford an enesulfonamide, enamine/imine isomerization, and Pd‐catalyzed asymmetric hydrogenation.