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Dynamic Kinetic Resolution Approach for the Asymmetric Synthesis of Tetrahydrobenzodiazepines Using Transfer Hydrogenation by Chiral Phosphoric Acid
Author(s) -
Horiguchi Kosaku,
Yamamoto Eri,
Saito Kodai,
Yamanaka Masahiro,
Akiyama Takahiko
Publication year - 2016
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.201601611
Subject(s) - substituent , kinetic resolution , phosphoric acid , chemistry , transfer hydrogenation , hydrogen bond , catalysis , kinetic energy , combinatorial chemistry , organic chemistry , enantioselective synthesis , molecule , physics , quantum mechanics , ruthenium
Asymmetric synthesis of tetrahydrobenzodiazepines was achieved by transfer hydrogenation of dihydrobenzodiazepines with benzothiazoline having a hydrogen‐bonding donor substituent by means of a newly synthesized chiral phosphoric acid. This method was applicable to various racemic dihydrobenzodiazepines to give the corresponding products in good yields with excellent diastereoselectivities and enantioselectivities taking advantage of the dynamic kinetic resolution. Furthermore, the effect of bulky substituent at 3,3′‐position on the catalyst and hydrogen‐bonding donor substituent on benzothiazoline was fully elucidated by the theoretical study.