Oxidative Catalytic Spiroketalization Leading to Diastereoselective Synthesis of Spiro[benzofuran-2,1′-isochromene]s

Jiang Kai Qiu, Wen Juan Hao, Guigen Li, Bo Jiang

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

A new one-pot, two-step silver-catalyzed spiroketalization of the in-situ generated quinone imine ketals (QIKs) with β-alkynyl ketones has been established, enabling multiple C−O and C−C bond-forming reactions to access densely functionalized spiro[benzofuran-2,1′-isochromene] derivatives with generally good yields. The use of β-alkynyl ketones bearing alkyl and aryl groups located at the α-position of the carbonyl group could lead to highly diastereoselective spiro[chromane-2,1′-isochromene] derivatives. The reaction features broad substrate scope, mild oxidative catalytic conditions and excellent diastereoselectivity. (Figure presented.).

Original languageEnglish
Pages (from-to)1182-1192
Number of pages11
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number6
DOIs
StatePublished - Mar 20 2018

Keywords

  • 1,4-Addition
  • Benzannulated 5,6-Spiroketals
  • Diastereoselectivity
  • Silver Catalysis
  • Spiroketalization

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