Catalytic Asymmetric Ring-Opening Reactions of Aziridines with 3-Aryl-Oxindoles

Chemistry, an Asian Journal
Linqing WangRui Wang

Abstract

A highly enantioselective ring-opening alkylation reaction between 3-aryl-oxindole and N-(2-picolinoyl) aziridine has been realized for the first time. The reaction is efficiently mediated by a simple in-situ-generated magnesium catalyst and 3,3'-fluorinated-BINOL (BINOL=1,1'-binaphthalene-2,2'-diol) has been identified as a powerful chiral ligand. Notably, the fluorine atom on the chiral ligand plays a key role in providing the desired chiral 3-alkyl-3-aryl oxindoles with excellent enantioselectivities.

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Citations

Jun 18, 2016·Chemical Communications : Chem Comm·Dan LiDongxu Yang
Jan 21, 2017·Chemical Communications : Chem Comm·Noriyuki ShiomiShuichi Nakamura
May 18, 2017·Organic & Biomolecular Chemistry·Hélène Pellissier
May 8, 2018·Molecular Diversity·Rabia AkhtarSameera Saleem
Apr 18, 2020·Inorganic Chemistry·David Van CraenAmar H Flood
Oct 6, 2021·Organic Letters·Kinney Van HeckeJeremy B Morgan

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