Journal
ORGANIC LETTERS
Volume 20, Issue 11, Pages 3156-3160Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00821
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Funding
- National Natural Science Foundation of China [21672027, 21402014]
- QingLan Project of Jiangsu Province
- Six-Talent Peaks Program of Jiangsu
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A range of novel (poly)cyclic alkaloids incorporating an unprecedented 1,S-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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