1,3‐Sulfinate Migration Triggered by α‐Imino Carbene and Divergent Zwitterion Cyclization: Synthesis of Cyclopropane, Dihydropyrrole, and Azepane Ring Systems

Author:

Xu Huaping12,Kong Xiaoyu1,Cen Mengjie1,Xu Ze‐Feng1ORCID,Duan Shengguo1ORCID,Li Chuan‐Ying1ORCID

Affiliation:

1. Department of Chemistry Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province Zhejiang Sci-Tech University Xiasha West Higher Education District Hangzhou 310018 P. R. China

2. School of Materials Science and Engineering Zhejiang Sci-Tech University Xiasha West Higher Education District Hangzhou 310018 P. R. China

Abstract

AbstractCyclopropane, dihydropyrrole, and azepane ring systems were synthesized conveniently from sulfinate‐tethered triazoles. The divergent synthetic strategy started with the unique 1,3‐sulfinate migration of an α‐imino carbene. The efficient reaction allowed control of the zwitterion bearing multiple reactive sites depending on the increased stability of the resulting carbocation and anion. The sulfinate was converted to a sulfone after the group migration, and a stable anion bearing two electron‐withdrawing groups was thus formed. Catalytic amounts of iodide acted as a switch for the synthesis of cyclopropanes and dihydropyrroles. The reaction merits including readily available substrates, mild reaction conditions, and excellent functional group compatibility qualified this protocol a possible synthetic tool for cyclic compounds, especially for N‐heterocycles.

Funder

National Natural Science Foundation of China

Natural Science Foundation of Zhejiang Province

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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