Rhodium(I)-catalyzed asymmetric carbene insertion into B-H bonds: highly enantioselective access to functionalized organoboranes.
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.
†State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.
Diao
D
Chen
‡Department of Chemistry, Shanghai University, Shanghai 200444, China.
Xu
X
Zhang
†State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.
Wei-Yi
WY
Qi
‡Department of Chemistry, Shanghai University, Shanghai 200444, China.
Bin
B
Xu
†State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.
Ming-Hua
MH
Xu
D000586:Amination; D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D001880:Boranes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D001391:Azo Compounds; D001880:Boranes; D008024:Ligands; C030011:carbene; D012238:Rhodium; D008697:Methane