Asymmetric Diels–Alder reaction between furans and propiolates

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

研究成果: Article査読

抄録

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.

本文言語English
論文番号153075
ジャーナルTetrahedron Letters
72
DOI
出版ステータスPublished - 2021 5 25

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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