Base-Promoted [3 + 2] and [2 + 1] Annulation of Alkenyl Sulfonium Salts to Access 2-Oxazolines and Cyclopropanes

A base-promoted annulation reaction of alkenyl sulfonium salts with amides and acetophenones has been readily developed. This method enables the regioselective synthesis of various 2-oxazoline and cyclopropane compounds in good to high yields with a wide substrate scope and high functional group tolerance. Notably, this practical [3 + 2] or [2 + 1] annulation strategy circumvents the need for transition-metal catalysts, strong oxidants, and harsh reaction conditions, thereby enhancing its appeal in organic synthesis.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-01-06
DOI
https://doi.org/10.1021/acs.joc.5c02518
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
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article

Base-Promoted [3 + 2] and [2 + 1] Annulation of Alkenyl Sulfonium Salts to Access 2-Oxazolines and Cyclopropanes

Shan-Shan 뺤깿 Tang, Limei Duan, Ding Luo, Long-Yong Xie et al.
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

Base-Promoted [3 + 2] and [2 + 1] Annulation of Alkenyl Sulfonium Salts to Access 2-Oxazolines and Cyclopropanes

Shan-Shan 뺤깿 Tang, Limei Duan, Ding Luo, Long-Yong Xie, Sha Peng
article en

Abstract

A base-promoted annulation reaction of alkenyl sulfonium salts with amides and acetophenones has been readily developed. This method enables the regioselective synthesis of various 2-oxazoline and cyclopropane compounds in good to high yields with a wide substrate scope and high functional group tolerance. Notably, this practical [3 + 2] or [2 + 1] annulation strategy circumvents the need for transition-metal catalysts, strong oxidants, and harsh reaction conditions, thereby enhancing its appeal in organic synthesis.

The Journal of Organic ChemistryVol. 91(2)
Hunan University of Science and Engineering (CN), Bioengineering Center (RU)
Openalex Percentile: Top 95%
Sulfur-Based Synthesis Techniques
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