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 |
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論文番号 | 153075 |
ジャーナル | Tetrahedron Letters |
巻 | 72 |
DOI | |
出版ステータス | Published - 2021 5月 25 |
ASJC Scopus subject areas
- 生化学
- 創薬
- 有機化学