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Chiral Phosphoric‐Acid‐Catalyzed Transfer Hydrogenation of Ethyl Ketimine Derivatives by Using Benzothiazoline
Author(s) -
Saito Kodai,
Horiguchi Kosaku,
Shibata Yukihiro,
Yamanaka Masahiro,
Akiyama Takahiko
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402763
Subject(s) - transfer hydrogenation , reductive amination , enantioselective synthesis , chemistry , phosphoric acid , noyori asymmetric hydrogenation , propiophenone , catalysis , organic chemistry , ketone , alkyl , hydrogen , combinatorial chemistry , ruthenium
Chiral phosphoric acid catalyzed transfer hydrogenation of ketimines derived from propiophenone derivatives and reductive amination of alkyl ethyl ketone derivatives were extensively examined in the presence of two representative hydrogen donors. The excellent enantioselective transfer hydrogenation was achieved by use of benzothiazoline as a hydrogen donor. The theoretical studies elucidated that the unsymmetrical structure of benzothiazoline plays an important role in high enantioselective hydrogenation.