Intramolecular Imino-ene Reaction of 2H-azirines with Alkenes: Rapid Construction of Spiro NH Aziridines from Vinyl Azides

Organic Letters
Tai-Shang LiuHua-Dong Xu

Abstract

A range of novel (poly)cyclic alkaloids incorporating an unprecedented 1,5-diazaspiro[2.4]heptane core that carry a spiro NH aziridine moiety and a 7-vinyl group are constructed from the thermal reaction of vinyl azides with tethered alkenes. Vinyl azides are converted to 2H-azirines in situ, which serve as enophiles for intramolecular imino-ene reactions with suitable alkenes. High stereoselectivity and specificity have been achieved for this novel intramolecular imino-ene reaction of azirines.

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Citations

Jun 6, 2019·Organic & Biomolecular Chemistry·Satheesh BorraRam Awatar Maurya
Feb 13, 2020·Organic & Biomolecular Chemistry·Kizhakkan Thiruthi AshithaSasidhar Balappa Somappa
Apr 17, 2020·Chemical Communications : Chem Comm·Zhongzhi ZhuYibiao Li

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