Enantioselective Skeletal Transformation of 1,2,3-Thiadiazoles to Dihydrothiophenes

Herein, we report the asymmetric Rh-catalyzed NN to CC diatomic swap of 1,2,3-thiadiazoles with terminal alkenes, producing enantiopure 2,3-dihydrothiophenes in excellent yields (up to 99%) and good enantioselectivities (86:14-92:8) in most cases. Wide substrate scope, excellent functionality tolerance, and structural modifications of natural and drug molecules are demonstrated.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-23
DOI
https://doi.org/10.1021/acs.joc.5c02611
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.94
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article

Enantioselective Skeletal Transformation of 1,2,3-Thiadiazoles to Dihydrothiophenes

Zhanhui Yang, Cunzhi Chen, Jiaxi Xu, DU Hong-guang et al.
1 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
0.94
article

Enantioselective Skeletal Transformation of 1,2,3-Thiadiazoles to Dihydrothiophenes

Zhanhui Yang, Cunzhi Chen, Jiaxi Xu, DU Hong-guang, Xinru Zhang
article en
1 citations

Abstract

Herein, we report the asymmetric Rh-catalyzed NN to CC diatomic swap of 1,2,3-thiadiazoles with terminal alkenes, producing enantiopure 2,3-dihydrothiophenes in excellent yields (up to 99%) and good enantioselectivities (86:14-92:8) in most cases. Wide substrate scope, excellent functionality tolerance, and structural modifications of natural and drug molecules are demonstrated.

The Journal of Organic ChemistryVol. 91(1)
Beijing University of Chemical Technology (CN)
Openalex Percentile: Top 19%
Catalytic C–H Functionalization Methods
0.94
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