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COAP/Pd-Catalyzed Linear Asymmetric Allylic Alkylation for Optically Active 3,3-Disubstituted Oxindole Derivatives with a Four-Carbon Amino Side Chain

Wenkai Liu, Bailin Wang, Sheng‐Suo Zhou, Jun-Hao Shen, Zheng Wang, Xing‐Wang Wang

2022Organic Letters20 citationsDOI

Abstract

An asymmetric linear selective allylic alkylation of vinylaziridines with 3-aryl oxindoles has been developed by using a chiral oxamide-phosphine (COAP-Bn-OMe-p)/palladium complex in methanol, which furnished a wide variety of 3,3-disubstituted oxindole derivatives in good yields with excellent regio- and enantioselectivities.

Topics & Concepts

ChemistryOxindoleTsuji–Trost reactionAllylic rearrangementCatalysisArylPalladiumPhosphineEnantioselective synthesisAsymmetric carbonAlkylationOptically activeCombinatorial chemistryStereochemistryOrganic chemistryAlkylAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis