De novo construction of chiral 3‑oxindoles via organocatalyzed enantioselective ortho-Friedel-Crafts addition/novel [1,2]-ester migration

Author:

Wang Yong1,Pi Chao1,Wu Yangjie1,Cui Xiuling1

Affiliation:

1. Zhengzhou University

Abstract

Abstract The de novo construction of chiral 3-hydroxyindolenines and 3-oxindoles from easily available starting materials has been highly desired. Meanwhile, the intermolecular enantioselective ortho-C-H addition to ketone carbonyl remains a long-standing challenge. Herein, an unprecedent enantioselective intermolecular direct ortho-Friedel-Crafts addition of primary aryl amine with 2,3-diketoesters to construct 3-hydroxyindolenines with a chiral tertiary alcohol has been disclosed. The following unusual [1,2]-ester migration provides a family of chiral 3-oxindoles in good to excellent yields with excellent enantio-selectivity.

Publisher

Research Square Platform LLC

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