Palladium‐Catalyzed Asymmetric Hydrogenolysis of  N ‐Sulfonyl Aminoalcohols via Achiral Enesulfonamide Intermediates | Zendy

Yu ChangBin | Zendy; Zhou YongGui | Zendy

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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.

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