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

Author:
Chen, Diao, Zhang, Xu, Qi, Wei-Yi, Xu, Bin, Xu, Ming-Hua
Source:
Journal of the American Chemical Society 2015 v.137 no.16 pp. 5268-5271
ISSN:
1520-5126
Subject:
carbonyl compounds, enantiomers, esters, ketones, ligands, rhodium
Abstract:
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.
Agid:
5409964