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

Author(s) Wu, C.Y.; Zhang, Y.F.; Xu, M.H.
Journal Org Lett
Date Published 2018 Mar 13
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.

DOI 10.1021/acs.orglett.8b00289
ISSN 1523-7052
Citation Wu C-, Zhang Y-, Xu M-. Ligand-Controlled Rhodium-Catalyzed Site-Selective Asymmetric Addition of Arylboronic Acids to α,β-Unsaturated Cyclic N-Sulfonyl Ketimines. Org Lett. 2018.

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