Premium
Rhodium‐Catalyzed Asymmetric Hydrogenation of Unprotected NH Imines Assisted by a Thiourea
Author(s) -
Zhao Qingyang,
Wen Jialin,
Tan Renchang,
Huang Kexuan,
Metola Pedro,
Wang Rui,
Anslyn Eric V.,
Zhang Xumu
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404570
Subject(s) - rhodium , asymmetric hydrogenation , thiourea , chemistry , imine , phosphine , catalysis , yield (engineering) , medicinal chemistry , organic chemistry , enantioselective synthesis , materials science , metallurgy
Asymmetric hydrogenation of unprotected NH imines catalyzed by rhodium/bis(phosphine)‐thiourea provided chiral amines with up to 97 % yield and 95 % ee . 1 H NMR studies, coupled with control experiments, implied that catalytic chloride‐bound intermediates were involved in the mechanism through a dual hydrogen‐bonding interaction. Deuteration experiments proved that the hydrogenation proceeded through a pathway consistent with an imine.