COAP‐Palladium‐Catalyzed Asymmetric Linear Allylic Alkylation of Vinyl Benzoxazinanones for Multifunctional 3,3′‐Disubstituted Oxindole Derivatives

Author:

Shen Jun‐Hao1,Zhou Sheng‐Suo1,Wang Bai‐Lin1,Liu Wen‐Kai1,Wang Zheng2,Wang Xing‐Wang1ORCID

Affiliation:

1. Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University Suzhou 215123 People's Republic of China

2. State Key Laboratory of Organometallic Chemistry Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 People's Republic of China

Abstract

AbstractA Pd‐catalyzed enantioselective linear‐allylic alkylation of vinyl benzoxazinanones with a series of 3‐substituted oxindoles was reported in the presence of a chiral oxamide‐phosphine ligand (COAP−Bn) under mild reaction conditions. A series of optically active multifunctional 3,3′‐disubstituted oxindole derivatives bearing a quaternary stereogenic center and a linear aryl amino side chain were respectively obtained in 55–98% yields with 96–99% ee for 3‐(hetero)aryl substituted oxindoles. The developed protocol demonstrates that the COAP ligands could serve as a privileged chiral ligand to construct diverse chiral 3,3‐disubstituted oxindole compounds with various quaternary stereogenic centers, such as aza‐, thio‐ or all‐carbon quaternary stereogenic centers. The salient features of the method include broad substrate scope, N‐protecting group free, base‐free, and high regio‐ and enantioselectivity.magnified image

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry

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