Asymmetric Diels-Alder reaction between furans and propiolates

TETRAHEDRON LETTERS

卷:72

Article

Ogura, Akihiro¹  Ito, Taisuke¹  Moriya, Koujiro¹  Horigome, Hiroki¹  Takao, Ken-ichi¹ 

[1] Keio Univ, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

关键词: Diels-Alder reaction;    Furan;    Propiolate;   

DOI  :  10.1016/j.tetlet.2021.153075

来源: Elsevier

【 摘 要 】

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. (C) 2021 Elsevier Ltd. All rights reserved.

【 授权许可】

Free