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Ir‐Catalyzed Asymmetric Hydrogenation of α‐Alkylidene β‐Lactams and Cyclobutanones
Author(s) -
Xia Jingzhao,
Nie Yu,
Yang Guoqiang,
Liu Yangang,
Gridnev Ilya D.,
Zhang Wanbin
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800088
Subject(s) - chemistry , ring (chemistry) , catalysis , stereoselectivity , substrate (aquarium) , scope (computer science) , optically active , combinatorial chemistry , asymmetric hydrogenation , enantioselective synthesis , stereochemistry , medicinal chemistry , organic chemistry , oceanography , computer science , programming language , geology
Chiral β‐lactams and cyclobutanones are present in numerous natural and pharmaceutical products. The stereoselective construction of chiral four‐membered cyclic compounds is an ongoing challenge for the chemical community. Herein, we report a highly stereocontrolled construction of four‐membered ring (mini‐sized) β‐lactams and cyclobutanones via an Ir/ In‐BiphPHOX ‐catalyzed asymmetric hydrogenation, providing the corresponding optically active four‐membered ring carbonyl products bearing an α‐chiral carbon center with excellent yields (up to 99%) and enantioselectivities (up to 98%) under mild reaction conditions (1.0—2.5 bar H 2 for 1.0—10 h). The reaction presents wide substrate scope. Diverse transformations of the catalyzed products were also conducted to show the potential utility of this protocol.