Open AccessCu-Catalyzed Asymmetric Aminoboration of E-Vinylarenes with pivZPhos as the Ligand
Author(s) -
Linglin Wu,
Olga V. Zatolochnaya,
Bo Qu,
Lucille A. Wells,
Marisa C. Kozlowski,
Chris H. Senanayake,
Jinhua J. Song,
Yongda Zhang
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b03328
Subject(s) - chemistry , enantioselective synthesis , ligand (biochemistry) , catalysis , adduct , chiral ligand , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , receptor , biochemistry
A Cu-catalyzed enantioselective aminoboration of E -vinylarenes with piv ZPhos as a ligand is reported. Enantioenriched aminoborates are prepared with excellent regio- and enantioselectivities up to >99:1 er under the optimized conditions. The utility of the current method was further established by rapid conversion of an adduct to a chiral benzo[ f ][1,4]oxazepine. A model for the stereochemistry of the asymmetric aminoboration process, which agrees with the experimental outcomes, was generated by computational analysis of the systems.