Catalytic ring expansion of vinyl oxetanes: Asymmetric synthesis of dihydropyrans using chiral counterion catalysis

Boying Guo, Gregg Schwarzwalder, Jon T. Njardarson

Research output: Contribution to journalArticle

50 Scopus citations

Abstract

Acid Showdown! The first catalytic ring expansion of vinyl oxetanes to 3,6-dihydro-2H-pyrans is described. Copper(II) triflate emerged as the best catalyst for this new transformation, which has broad scope as demonstrated by the eighteen examples included. The symmetric vinyl oxetane substrate can be asymmetrically desymmetrized when using either chiral Lewis or Brønsted acids as catalysts.

Original languageEnglish (US)
Pages (from-to)5675-5678
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number23
DOIs
StatePublished - Jun 4 2012

Keywords

  • chiral counterions
  • copper
  • homogeneous catalysis
  • ring expansion
  • vinyl oxetanes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Catalytic ring expansion of vinyl oxetanes: Asymmetric synthesis of dihydropyrans using chiral counterion catalysis'. Together they form a unique fingerprint.

  • Cite this