4.8 Article

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

Journal

ORGANIC LETTERS
Volume 19, Issue 14, Pages 3831-3834

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01705

Keywords

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Funding

  1. NSFC [21232004, 21472071, 21602087]
  2. PAPD of Jiangsu Higher Education Institutions
  3. Outstanding Youth Fund of JSNU [YQ2015003]
  4. NSF of Jiangsu Province [BK20151163, BK20160212]
  5. Qing Lan Project
  6. NSF of Jiangsu Education Committee [15KJB150006]

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A new Ag/Bronsted acid to-catalyzed spiroketalization of beta-alkynyl ketones with parq-quincine methides (p-QMs) has been: established, enabling multiple C-C and C-O bond-forming events to access densely functionalized spiro[chrcimane-2,1'-isochromene]. derivatives with generally excellent diastereoselectivity and good yields. A reasonable mechanism for forming these 6,6-dibenzannulated spiraetals involving. 6-endo-dig oxo-cyclization and 1,6-addition-cyclization cascades is proposed.

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