Carbene-Catalyzed [4 + 2] Annulation of 2H‑Azirine-2-carboxaldehydes with Ketones via Azolium Aza-Dienolate Intermediate

Carbene-Catalyzed [4 + 2] Annulation of 2H‑Azirine-2-carboxaldehydes with Ketones via Azolium Aza-Dienolate Intermediate

A new carbene-catalyzed [4 + 2] annulation of 2H-azirine-2-carbaldehydes with ketones was developed, thus providing the 2,3-dihydro-6H-1,3-oxazin-6-one core structures with broad scope and good to excellent yields. Notably, the azolium aza-dienolates generated from the addition of NHCs to 2H-azirine...

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Veröffentlicht in:Organic letters 2018-12, Vol.20 (23), p.7641-7644
Hauptverfasser: Peng, Qiupeng, Zhang, Bei, Xie, Yangxi, Wang, Jian
Format: Artikel
Sprache:eng
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Zusammenfassung:A new carbene-catalyzed [4 + 2] annulation of 2H-azirine-2-carbaldehydes with ketones was developed, thus providing the 2,3-dihydro-6H-1,3-oxazin-6-one core structures with broad scope and good to excellent yields. Notably, the azolium aza-dienolates generated from the addition of NHCs to 2H-azirines are first uncovered.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03378