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Asymmetric Hydrogenation of Isoquinolinium Salts Catalyzed by Chiral Iridium Complexes: Direct Synthesis for Optically Active 1,2,3,4‐Tetrahydroisoquinolines
Author(s) -
Iimuro Atsuhiro,
Yamaji Kenta,
Kandula Sathaiah,
Nagano Takuto,
Kita Yusuke,
Mashima Kazushi
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.201207748
Subject(s) - iridium , salt (chemistry) , enantioselective synthesis , asymmetric hydrogenation , enantiomer , catalysis , chemistry , combinatorial chemistry , optically active , enantiomeric excess , medicinal chemistry , organic chemistry
The salt makes the difference : In the presence of a chiral iridium catalyst, 1‐ and 3‐substituted as well as 1,3‐disubstituted isoquinolinium salts can be hydrogenated, giving the corresponding 1,2,3,4‐tetrahydroisoquinolines in high enantiomeric excess after a basic workup (see scheme). This protocol is applicable to the synthesis of the prescription drug solifenacin.