Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins

Mei Huey Lin, Yi Syuan Li, Chung Kai Kuo, Chung Hao Chen, Yen Chih Huang, Kung Yu Liang, Yu Chun Chen, Chang Hsien Tsai, Tsung Hsun Chuang

研究成果: Article

6 引文 斯高帕斯(Scopus)

摘要

A procedure has been developed for the concise synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr3-mediated SN2′-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular Diels-Alder reaction of the formed ene-diene to generate the target hexahydro-1H-isoindole.

原文English
頁(從 - 到)2462-2466
頁數5
期刊Journal of Organic Chemistry
80
發行號4
DOIs
出版狀態Published - 2015 二月 20

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

指紋 深入研究「Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins」主題。共同形成了獨特的指紋。

  • 引用此

    Lin, M. H., Li, Y. S., Kuo, C. K., Chen, C. H., Huang, Y. C., Liang, K. Y., Chen, Y. C., Tsai, C. H., & Chuang, T. H. (2015). Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins. Journal of Organic Chemistry, 80(4), 2462-2466. https://doi.org/10.1021/acs.joc.5b00072