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Paper | Regular issue | Vol 106, No. 3, 2023, pp.465-478
Published online, 8th February, 2023
DOI: 10.3987/COM-23-14811
■ Organic Base-Catalyzed Cascade Reaction of Electron-Deficient Cyclopentadienone with Prop-2-yn-1-ols: Formation of 3-Methylenetetrahydrofuran Ring Condensed with Cyclopentenone

Koki Yamaguchi*

*Faculty of Pharmaceutical Sciences, Sojo University, 4-22-1 Ikeda, Nishi-ku, Kumamoto 860-0082, Japan

Abstract

2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone (1a) reacts with prop-2-yn-1-ols (2) in the presence of 1,4-diazabicyclo[2.2.2]octane at room temperature to produce bicyclic carbocycles (4) in moderate yields, as well as tetracyclic carbocycle (5). The bicyclic carbocycle, which has a 3-methylenetetrahydrofuran moiety, is derived from the anionic cyclization of the 1,4-adducts of 1a and 2 onto a non-activated alkyne. The mechanism of the cascade reaction was discussed based on the density functional theory calculations and the X-ray crystallographic analysis.