Rhodium(I)-Catalyzed Asymmetric Carbene Insertion into B–H Bonds: Highly Enantioselective Access to Functionalized Organoboranes | Zendy

Chen Diao | Zendy; Xu Zhang | Zendy; Weiyi Qi | Zendy; Bin Xu | Zendy; MingHua Xu | Zendy

Open Access

Rhodium(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 , enantioselective synthesis , rhodium , borane , catalysis , diazo , ligand (biochemistry) , amine gas treating , migratory insertion , insertion reaction , medicinal chemistry , adduct , diene , combinatorial chemistry , organic chemistry , stereochemistry , biochemistry , receptor , natural rubber

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.

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