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Ligand-Controlled Rhodium-Catalyzed Site-Selective Asymmetric Addition of Arylboronic Acids to α,β-Unsaturated Cyclic N-Sulfonyl Ketimines

Author:
Wu, Chun-Yan, Zhang, Yu-Fang, Xu, Ming-Hua
Source:
Organic letters 2018 v.20 no.7 pp. 1789-1793
ISSN:
1523-7052
Subject:
acids, amines, amino acid derivatives, chemical reactions, chemical structure, ketimines, ligands, olefin, regioselectivity
Abstract:
A site-selective rhodium-catalyzed asymmetric 1,4-/1,2-addition of arylboronic acids to challenging α,β-unsaturated cyclic ketimines was realized through a ligand-controlled strategy. By employing different chiral olefin ligands, a ligand-controlled switch in the reaction regioselectivity was attained for the first time. The reactions allow the synthesis of highly valuable α,α-disubstituted chiral allylic amines and enantioenriched 1,4-adducts. Further product transformation provided easy access to various quaternary carbon-containing chiral amines and amino acid derivatives bearing multifunctional groups.
Agid:
6083642