Stereoselective preparation of conjugated (Z)-1,3-enynes by dehydration reactions of allenic bromohydrins and the use of the enynes in base-mediated tandem allylation ene-carbocyclization reactions with β-ketoesters

Mei Huey Lin, Yu Chun Chen, Shih Hao Chiu, Kung Yu Liang, Yi Lin Lee, Tsung Hsun Chuang

研究成果: Article

2 引文 斯高帕斯(Scopus)

摘要

A procedure has been developed for the concise, stereoselective synthesis of (Z)-5-bromo-4-aryl-pent-3-en-1-ynes through Sc(OTf)3 catalyzed dehydration reactions of allenic bromohydrins. (Z)-1,3-Enynes are transformed to methylenecyclopentenes when subjected to a sequential, one-pot process involving base mediated allylation reactions with ethyl acetoacetate followed by ene-carbocyclization reactions. An unprecedented rearrangement reaction involving 1,5-acyl migration takes place when the methylenecyclopentenes are treated with acid to form highly substituted cyclopentadienes.

原文English
頁(從 - 到)605-609
頁數5
期刊Organic and Biomolecular Chemistry
15
發行號3
DOIs
出版狀態Published - 2017 一月 1

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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