Asymmetric Hydrogenation of Isoquinolinium Salts Catalyzed by Chiral Iridium Complexes: Direct Synthesis for Optically Active 1,2,3,4-Tetrahydroisoquinolines

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 protoc...

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Published inAngewandte Chemie International Edition Vol. 52; no. 7; pp. 2046 - 2050
Main Authors Iimuro, Atsuhiro, Yamaji, Kenta, Kandula, Sathaiah, Nagano, Takuto, Kita, Yusuke, Mashima, Kazushi
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 11.02.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
asymmetric synthesis
Asymmetry
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Coordination Complexes - chemistry
Drugs
Hydrogenation
Iridium
Iridium - chemistry
isoquinolines
Optical activity
Physical Sciences
Science & Technology
Stereoisomerism
Synthesis
tetrahydroisoquinolines
Tetrahydroisoquinolines - chemical synthesis
Tetrahydroisoquinolines - chemistry
DIFLUORPHOS
isoquinolines
PYRIDINE-DERIVATIVES
QUINOLINES
hydrogenation
iridium
tetrahydroisoquinolines
ACID-DERIVATIVES
HIGHLY ENANTIOSELECTIVE HYDROGENATION
asymmetric synthesis
LIGANDS
QUINOXALINES
EFFICIENT
ACCESS
ALKALOIDS
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Summary: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.
Bibliography:This work was financially supported by the Core Research for Evolutional Science and Technology (CREST), the program of the Japan Science and Technology Agency (JST), and a Grant-in-Aid for Scientific Research on Innovative Areas, "Molecular Activation Directed toward Straightforward Synthesis", from the Ministry of Education, Culture, Sports, Science and Technology (MEXT).
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istex:D6338575716523D1EF7790DBBF9E0FB690E089D4
Core Research for Evolutional Science and Technology (CREST)
Japan Science and Technology Agency (JST)
ArticleID:ANIE201207748
Ministry of Education, Culture, Sports, Science and Technology (MEXT)
This work was financially supported by the Core Research for Evolutional Science and Technology (CREST), the program of the Japan Science and Technology Agency (JST), and a Grant‐in‐Aid for Scientific Research on Innovative Areas, “Molecular Activation Directed toward Straightforward Synthesis”, from the Ministry of Education, Culture, Sports, Science and Technology (MEXT).
KAKEN
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201207748