Catalytic Enantioselective Formal (3 + 3) Cycloaddition of 3-Halooxindoles with Pyridinium 1,4-Zwitterionic Thiolates

Organic Letters 2026

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Authors: Xue-Song Peng, Ting-Jia Sun, Wei Sun, Guo-Yin Sun, Yong You, Yingyue Zhang, Zhen‐Hua Wang, Jian-Qiang Zhao, Ming‐Qiang Zhou, Wei-Cheng Yuan
DOI: 10.1021/acs.orglett.6c00614
Cited by: 1
References: 51

Abstract

The first catalytic enantioselective formal (3 + 3) cycloaddition of pyridinium 1,4-zwitterionic thiolates with indol-2-ones, generated in situ from 3-halooxindoles and serving as C–C–O three-atom reaction components, was successfully developed. A series of optically pure indolenine-fused 2 H -1,4-oxathiines were obtained in moderate to good yields with high enantioselectivities using a catalyst system comprising a chiral tridentate Pybox ligand and Ni(acac) 2 . The products could be further converted to chiral 3-sulfenyl-3,3′-disubstituted oxindoles with stereoretention. This work also represents the first report on a catalytic asymmetric cycloaddition reaction involving pyridinium 1,4-zwitterionic thiolates.

Fields of Study & Subjects

Catalytic C–H Functionalization Methods Asymmetric Synthesis and Catalysis Sulfur-Based Synthesis Techniques

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
14
Pages
4433–4439
Publication date
31 March 2026
Language
EN