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

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, whic...

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Bibliographic Details
Published in:Organic letters 2018-06, Vol.20 (11), p.3156-3160
Main Authors: Liu, Tai-Shang, Zhou, Hao, Chen, Peng, Huang, Xiu-Rong, Bao, Lin-Qing, Zhuang, Chen-Lu, Xu, Qing-Song, Shen, Mei-Hua, Xu, Hua-Dong
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00821