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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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
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cited_by cdi_FETCH-LOGICAL-a345t-c02c666ffe83fe4ab5974d6e76d224f92cca5a33edd61200c9dec8a750a6cc1e3
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container_end_page 3160
container_issue 11
container_start_page 3156
container_title Organic letters
container_volume 20
creator Liu, Tai-Shang
Zhou, Hao
Chen, Peng
Huang, Xiu-Rong
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Zhuang, Chen-Lu
Xu, Qing-Song
Shen, Mei-Hua
Xu, Hua-Dong
description 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.
doi_str_mv 10.1021/acs.orglett.8b00821
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title Intramolecular Imino-ene Reaction of 2H-azirines with Alkenes: Rapid Construction of Spiro NH Aziridines from Vinyl Azides
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