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

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)605-609
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number3
DOIs
Publication statusPublished - 2017 Jan 1

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Allylation
Cyclopentanes
Dehydration
dehydration
preparation
Acids
acids
bromohydrins
scandium triflate
ethyl acetoacetate
synthesis

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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title = "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",
abstract = "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.",
author = "Lin, {Mei Huey} and Chen, {Yu Chun} and Chiu, {Shih Hao} and Liang, {Kung Yu} and Lee, {Yi Lin} and Chuang, {Tsung Hsun}",
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doi = "10.1039/c6ob02178f",
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publisher = "Royal Society of Chemistry",
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}

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

In: Organic and Biomolecular Chemistry, Vol. 15, No. 3, 01.01.2017, p. 605-609.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 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

AU - Lin, Mei Huey

AU - Chen, Yu Chun

AU - Chiu, Shih Hao

AU - Liang, Kung Yu

AU - Lee, Yi Lin

AU - Chuang, Tsung Hsun

PY - 2017/1/1

Y1 - 2017/1/1

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AB - 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.

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