Open AccessRhodium(I)-Catalyzed Asymmetric Carbene Insertion into B–H Bonds: Highly Enantioselective Access to Functionalized Organoboranes
Author(s) -
Chen Diao,
Xu Zhang,
Weiyi Qi,
Bin Xu,
MingHua Xu
Publication year - 2015
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.5b00892
Subject(s) - chemistry , carbene , rhodium , enantioselective synthesis , borane , diazo , migratory insertion , catalysis , insertion reaction , ligand (biochemistry) , amine gas treating , combinatorial chemistry , adduct , medicinal chemistry , organic chemistry , biochemistry , receptor
A unique rhodium(I)-catalyzed asymmetric B-H insertion of α-diazo carbonyl compounds with easily available amine-borane adducts was achieved using a newly developed C1-symmetric chiral diene as ligand. This first Rh(I)-carbene-directed B-H insertion example represents an attractive and promising approach for synthesis of highly enantioenriched organoboron compounds, allowing for the efficient construction of α-boryl esters and ketones with excellent enantioselectivities (up to 99% ee) under exceptionally mild conditions.