Intermolecular oxonium ylide mediated synthesis of medium-sized oxacycles

Daniel J. MacK, Lindsay A. Batory, Jon T. Njardarson

Research output: Contribution to journalArticle

29 Scopus citations

Abstract

Detailed in this account are our efforts toward efficient oxacycle syntheses. Two complementary approaches are discussed, with both employing chemoselective allyl ether activation and rearrangement as the key step. Vinyl substituted oxiranes and oxetanes provide a single step access to dihydropyrans and tetrahydrooxepines. Oxiranes proved to be poor substrates, while oxetanes were slightly better. An alternative approach using substituted allyl ethers proved successful and addressed the limitations encountered in the ring expansions.

Original languageEnglish (US)
Pages (from-to)378-381
Number of pages4
JournalOrganic Letters
Volume14
Issue number1
DOIs
StatePublished - Jan 6 2012

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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