An efficient organocatalytic reaction using 1,3-nitro enynes with 4-hydroxycoumarin and 4-hydroxy-6-methyl-2-pyrone to afford pyrano-annulated scaffolds in high yield (up to 88% yield) and excellent stereoselectivities (up to >20:1 dr and >99% ee) is described. The reaction proceeded through sequential conjugate addition, allene formation, intramolecular oxa-Michael 6-endo-dig cyclization and DABCO-catalyzed olefin isomerization. A kinetic profile for isomerization was established. The mechanism for the organocascade reaction was proposed according to requisite computational and mechanistic experimental studies.
|頁（從 - 到）||3098-3101|
|出版狀態||已發佈 - 2016 7月 1|
ASJC Scopus subject areas
指紋深入研究「Organocascade Synthesis of Annulated (Z)-2-Methylenepyrans: Nucleophilic Conjugate Addition of Hydroxycoumarins and Pyranone to Branched Nitro Enynes via Allene Formation/Oxa-Michael Cyclization/Alkene Isomerization Sequence」主題。共同形成了獨特的指紋。
CCDC 1465297: Experimental Crystal Structure Determination
Gurubrahamam, R. (Creator), Gao, B. (Creator), Chen, Y. M. (Creator), Chan, Y. (Creator), Tsai, M. B. (Creator) & Chen, K. (Creator), Unknown Publisher, 2016
DOI: 10.5517/ccdc.csd.cc1l5rn5, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1l5rn5&sid=DataCite