Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans

Jingqi Wang, Erika A. Crane, Karl A. Scheidt

Research output: Contribution to journalArticlepeer-review

68 Scopus citations

Abstract

A Brønsted acid-catalyzed Prins-type cyclization sequence to construct spirooxindole pyrans in high yields and excellent diastereoselectivity has been developed. The combination of a β-hydroxy dioxinone fragment and isatin dimethyl acetal generate oxa-spirooxindoles efficiently. These compounds are diversifiable scaffolds that tap into the rich chemistry of dioxinones.

Original languageEnglish (US)
Pages (from-to)3086-3089
Number of pages4
JournalOrganic Letters
Volume13
Issue number12
DOIs
StatePublished - Jun 17 2011

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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