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Iridium‐Catalyzed Asymmetric Hydrogenation of Substituted Pyridines
Author(s) -
Cadu Alban,
Upadhyay Puspesh K.,
Andersson Pher G.
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300160
Subject(s) - chemistry , iridium , piperidine , catalysis , asymmetric hydrogenation , recrystallization (geology) , noyori asymmetric hydrogenation , aromaticity , organic chemistry , enantioselective synthesis , combinatorial chemistry , medicinal chemistry , molecule , paleontology , biology
Asymmetric hydrogenation of ortho ‐substituted pyridines catalyzed by N,P‐ligated iridium is demonstrated. To facilitate this reaction, the aromaticity of the pyridines was weakened by forming N ‐iminopyridium ylides. The reactions give very high conversions, and after a single recrystallization, excellent ee of up to 98 % was obtained. This method lends itself to the synthesis of chiral piperidine building blocks.