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Switchable Stereoselectivity in Bromoaminocyclization of Olefins: Using Brønsted Acids of Anionic Chiral Cobalt(III) Complexes
Author(s) -
Jiang HuaJie,
Liu Kun,
Yu Jie,
Zhang Ling,
Gong LiuZhu
Publication year - 2017
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.201705066
Subject(s) - stereoselectivity , chemistry , diastereomer , enantioselective synthesis , cobalt , enantiomer , bifunctional , catalysis , brønsted–lowry acid–base theory , solvent , phase (matter) , organic chemistry , combinatorial chemistry
Brønsted acids of anionic chiral Co III complexes act as bifunctional phase‐transfer catalysts to shuttle the substrates across the solvent interface and control stereoselectivity. The diastereomeric chiral Co III ‐templated Brønsted acids, with the same chiral ligands, enabled a switch in the enantioselective bromoaminocyclization of olefins to afford the two enantiomers of 2‐substituted pyrrolidines with high enantioselectivities (up to 99:1 e.r.).