Asymmetric Diels–Alder reaction between furans and propiolates

Akihiro Ogura, Taisuke Ito, Koujiro Moriya, Hiroki Horigome, Ken ichi Takao

Research output: Contribution to journalArticlepeer-review

Abstract

We report the first asymmetric Diels–Alder reaction between furan and propiolates. Propiolate, a dienophile, was equipped with an Evans’ auxiliary and a sulfonyl group to control and facilitate diastereoselective cycloaddition. Treatment with furan as a diene and aluminium Lewis acid afforded a 7-oxabicyclo[2.2.1]heptadiene skeleton diastereoselectively. The origin of diastereoselectivity can be explained by chelation of aluminium center to carbonyl groups and oxygen of furan. Friedel–Crafts-type products were obtained when pyrrole was used as diene.

Original languageEnglish
Article number153075
JournalTetrahedron Letters
Volume72
DOIs
Publication statusPublished - 2021 May 25

Keywords

  • Diels–Alder reaction
  • Furan
  • Propiolate

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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