Enantioselective catalytic desymmetric ester aminolysis

Wen-Ya Zheng

1,#

Miao He

1,#

Hua Wu

1,*

Yu-Ping He

2,*

Affiliation +

*Correspondence to: Hua Wu, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai 200240, China. E-mail: hua.wu@sjtu.edu.cn
Yu-Ping He, Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444, China. E-mail: yuping_he@shu.edu.cn

Chiral Chem. 2027;3:202628. 10.70401/cc.2026.0037

Received: June 13, 2026Accepted: August 10, 2026Published: August 10, 2026

This manuscript is made available in its unedited form to allow early access to the reported findings. Further editing will be completed before final publication. As such, the content may include errors, and standard legal disclaimers are applicable.

Abstract

We report an organocatalytic enantioselective desymmetrization of 2-aminophenyl malonates enabled by intramolecular ester aminolysis. This protocol efficiently delivers C3-disubstituted oxindole derivatives bearing quaternary stereocenters under mild conditions with excellent chemo- and enantioselectivities. Notably, this reaction follows an acid-promoted dehydration pathway instead of an alcohol elimination pathway, which differs from conventional ester aminolysis reactions reported previously. Gram-scale synthesis and further derivatization of the resulting products demonstrate the synthetic utility of this transformation

Keywords

Desymmetrization, organocatalysis, quaternary stereocenter, ester aminolysis, oxindole

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Zheng WY, He M, Wu H, He YP. Enantioselective catalytic desymmetric ester aminolysis. Chiral Chem. 2027;3:202628. https://doi.org/10.70401/cc.2026.0037