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Iridium‐Catalyzed Asymmetric Hydrogenation of Pyridinium Salts
Author(s) -
Ye ZhiShi,
Chen MuWang,
Chen QingAn,
Shi Lei,
Duan Ying,
Zhou YongGui
Publication year - 2012
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.201205187
Subject(s) - pyridinium , iridium , chemistry , catalysis , substrate (aquarium) , reactivity (psychology) , biphenyl , combinatorial chemistry , organic chemistry , medicinal chemistry , medicine , oceanography , alternative medicine , pathology , geology
Highly efficient iridium‐catalyzed asymmetric hydrogenations of simple 2‐substituted pyridinium salts gives the chiral 2‐substituted piperidines with up to 93 % ee (see picture; cod=1,5‐cyclooctadiene; synphos=(5,6),(5′,6′)‐bis(ethylenedioxy)‐2,2′‐bis(diphenylphosphino)‐1,1′‐biphenyl). The key feature of this strategy is the activation of simple pyridines as the pyridinium salts, thus eliminating substrate inhibition and enhancing the reactivity.