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Iridium‐catalyzed Asymmetric Hydrogenation of Polycyclic Pyrrolo/Indolo[1,2‐ a ]quinoxalines and Phenanthridines
Author(s) -
Hu ShuBo,
Zhai XiaoYong,
Shen HongQiang,
Zhou YongGui
Publication year - 2018
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.201701450
Subject(s) - chemistry , iridium , catalysis , asymmetric hydrogenation , nitrogen atom , enantioselective synthesis , acetic anhydride , combinatorial chemistry , nitrogen , catalytic hydrogenation , organic chemistry , substrate (aquarium) , ring (chemistry) , oceanography , geology
Owing to the dehydrogenative rearomatization of hydrogenation product and poisoning effect of nitrogen atom, asymmetric hydrogenation of polycyclic nitrogen‐containing heteroaromatics is still a great challenge. Herein, through in situ protection of hydrogenation products with acetic anhydride to inhibit rearomatization and poisoning effect, a novel iridium‐catalyzed enantioselective hydrogenation of polycyclic nitrogen‐containing heteroaromatics – pyrrolo/indolo[1,2‐ a ]quinoxalines and phenanthridines – has been successfully developed, providing a facile access to chiral dihydropyrrolo/indolo[1,2‐ a ]quinoxalines and dihydrophenanthridines with up to 98% ee. The strategy features broad substrate scope, easy operation and potential medicinal application.