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Updated: Sep 10, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Phosphine-Catalyzed [3 + 2] Annulation of Sulfamidate-Derived 1-Azadienes: Synthesis of
Bo Wang1, Siyuan Ding1, Zhiyang Cui1
1Department of Chemistry, China Agricultural University, Beijing 100193, P. R. China.
Abstract:
This study presents a phosphine-catalyzed [3 + 2] annulation of sulfamidate imine-derived 1-azadienes with Morita-Baylis-Hillman (MBH) carbonates or allenoates, affording densely functionalized spiro[oxathiazole-cyclopentene] architectures under mild reaction conditions in generally high yields and excellent diastereoselectivities. Through a reductive ring contraction sequence of the spirocyclic thiosulfamide, valuable spirocyclic aziridine derivatives were accessed conveniently via both two-step and one-pot protocols.
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