Organic Letters
Organic Letters
5 years ago

Ag/Brønsted Acid Co-Catalyzed Spiroketalization of β-Alkynyl Ketones toward Spiro[chromane-2,1′-isochromene] Derivatives

Ag/Brønsted Acid Co-Catalyzed Spiroketalization of β-Alkynyl Ketones toward Spiro[chromane-2,1′-isochromene] Derivatives
Shu-Jiang Tu, Guigen Li, Bo Jiang, Wen-Juan Hao, Xin-Chan Lan, Shuai Liu, Ke Chen
A new Ag/Brønsted acid co-catalyzed spiroketalization of β-alkynyl ketones with para-quinone methides (p-QMs) has been established, enabling multiple C–C and C–O bond-forming events to access densely functionalized spiro[chromane-2,1′-isochromene] derivatives with generally excellent diastereoselectivity and good yields. A reasonable mechanism for forming these 6,6-dibenzannulated spiroketals involving 6-endo-dig oxo-cyclization and 1,6-addition-cyclization cascades is proposed.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01705

DOI: 10.1021/acs.orglett.7b01705

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