Palladium-Catalyzed Asymmetric Benzylation of 3-Aryl Oxindoles
- 20 October 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (44), 15534-15536
- https://doi.org/10.1021/ja1079755
Abstract
Herein we report palladium-catalyzed asymmetric benzylic alkylation with 3-aryl oxindoles as prochiral nucleophiles. Proceeding analogously to asymmetric allylic alkylation, asymmetric benzylation occurs in high yield and enantioselectivity for a variety of unprotected 3-aryl oxindoles and benzylic methyl carbonates using chiral bisphosphine ligands. This methodology represents a novel asymmetric carbon−carbon bond formation between a benzyl group and a prochiral nucleophile to generate a quaternary center.This publication has 24 references indexed in Scilit:
- Enantiodivergence in alkylation of 1-(6-methoxynaphth-2-yl)ethyl acetate by potassium dimethyl malonate catalyzed by chiral palladium-DUPHOS complexTetrahedron: Asymmetry, 2010
- Catalytic Transformations of Benzylic Carboxylates and CarbonatesSynthesis, 2009
- Asymmetric palladium-catalyzed benzylic nucleophilic substitution: high enantioselectivity with the DUPHOS family ligandsTetrahedron: Asymmetry, 2005
- Palladium-Catalyzed Nucleophilic Benzylic Substitutions of Benzylic EstersJournal of the American Chemical Society, 2003
- Asymmetric Transition-Metal-Catalyzed Allylic Alkylations: Applications in Total SynthesisChemical Reviews, 2003
- Palladium-Catalyzed Asymmetric Alkylation of Ketone EnolatesJournal of the American Chemical Society, 1999
- Asymmetric Alkylation of β-KetoestersJournal of the American Chemical Society, 1997
- Asymmetric Transition Metal-Catalyzed Allylic AlkylationsChemical Reviews, 1996
- Asymmetric palladium-catalyzed nucleophilic substitution of racemic 1-naphthylethyl estersTetrahedron: Asymmetry, 1995
- Palladium-catalyzed nucleophilic substitution of napht hylmethyl and 1-naphthylethyl estersTetrahedron Letters, 1992