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Iridium‐Catalyzed Asymmetric Hydrogenation of Unsaturated Piperazin‐2‐ones
Author(s) -
Wang Yanzhao,
Liu Yuanyuan,
Li Kun,
Yang Guoqiang,
Zhang Wanbin
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700175
Subject(s) - iridium , chemistry , ruthenocene , ligand (biochemistry) , catalysis , binap , asymmetric hydrogenation , oxazoline , planar chirality , phosphine , chiral ligand , noyori asymmetric hydrogenation , medicinal chemistry , substrate (aquarium) , enantioselective synthesis , organic chemistry , combinatorial chemistry , biochemistry , polymer , receptor , oceanography , geology , metallocene , polymerization
Two different iridium catalyst systems, generated from the ruthenocene‐based phosphine‐oxazoline ligand t Bu‐mono‐RuPHOX or the diphosphine ligand BINAP, were developed for the asymmetric hydrogenation of 5,6‐dihydropyrazin‐2(1 H )‐ones, affording chiral piperazin‐2‐ones in good yields and with moderate to good ee s. Different catalytic behaviors for the hydrogenation of these types of substrate were observed with these two catalyst systems. Our t Bu‐mono‐RuPHOX ligand, which bears a ruthenocene scaffold with planar chirality, was found to be the best ligand for the [Ir(L)(COD)]BArF catalyst system, affording the desired products with up to 94% ee .