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Catalytic Radical Process for Enantioselective Amination of C(sp 3 )−H Bonds
Author(s) -
Li Chaoqun,
Lang Kai,
Lu Hongjian,
Hu Yang,
Cui Xin,
Wojtas Lukasz,
Zhang X. Peter
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201808923
Subject(s) - enantioselective synthesis , amination , chemoselectivity , chemistry , catalysis , reactivity (psychology) , stereoselectivity , combinatorial chemistry , organic chemistry , stereochemistry , medicine , alternative medicine , pathology
A new catalytic radical system involving Co II ‐based metalloradical catalysis is effective in activating sulfamoyl azides for enantioselective radical 1,6‐amination of C(sp 3 )−H bonds, affording six‐membered chiral heterocyclic sulfamides in high yields with excellent enantioselectivities. The Co II ‐catalyzed C−H amination features an unusual degree of functional‐group tolerance and chemoselectivity. The unique reactivity and stereoselectivity is attributed to the underlying stepwise radical pathway. The resulting optically active cyclic sulfamides can be readily converted into synthetically useful chiral 1,3‐diamine derivatives without loss in enantiopurity.