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The Use of Phosphite‐Type Ligands in the Ir‐Catalyzed Asymmetric Hydrogenation of Heterocyclic Compounds
Author(s) -
Lyubimov Sergey E.,
Ozolin Dmitry V.,
Ivanov Pavel Yu,
Melman Artem,
Velezheva Valeriya S.,
Davankov Vadim A.
Publication year - 2014
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22267
Subject(s) - chemistry , carbazole , asymmetric hydrogenation , catalysis , chirality (physics) , catalytic hydrogenation , hydrochloride , base (topology) , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , enantioselective synthesis , mathematical analysis , chiral symmetry breaking , physics , mathematics , quantum mechanics , quark , nambu–jona lasinio model
A series of chiral phosphite‐type ligands was tested in asymmetric Ir‐catalyzed hydrogenation of quinolines and 2,4,5,6‐tetrahydro‐1H‐pyrazino(3,2,1‐ j , k )carbazole. Hydrogenation of quinaldine hydrochloride provided superior enantioselectivity up to 65% ee compared to quinaldine free base. The ligands were tested for the first time in the asymmetric Ir‐Ircatalyzed hydrogenation of 2,4,5,6‐tetrahydro‐1H‐pyrazino(3,2,1‐ j , k )carbazole yielding the antidepressant drug, pirlindole. Chirality 26:56–60, 2013 . © 2013 Wiley Periodicals, Inc.
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