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Copper‐Catalyzed Enantioselective Markovnikov Protoboration of α‐Olefins Enabled by a Buttressed N‐Heterocyclic Carbene Ligand
Author(s) -
Cai Yuan,
Yang XinTuo,
Zhang ShuoQing,
Li Feng,
Li YuQing,
Ruan LinXin,
Hong Xin,
Shi ShiLiang
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.201711229
Subject(s) - markovnikov's rule , enantioselective synthesis , carbene , chemistry , regioselectivity , steric effects , catalysis , ligand (biochemistry) , combinatorial chemistry , organic chemistry , copper , biochemistry , receptor
Reported is a highly enantioselective copper‐catalyzed Markovnikov protoboration of unactivated terminal alkenes. A variety of simple and abundant feedstock α‐olefins bearing a diverse array of functional groups and heterocyclic substituents can be used as substrates, and the reaction proceeds under mild reaction conditions at ambient temperature to provide expedient access to enantioenriched alkylboronic esters in good regioselectivity and with excellent enantiocontrol. Critical to the success of the protocol was the development and application of a novel, sterically hindered N‐heterocyclic carbene, ( R , R , R , R )‐ANIPE, as the ligand for copper.