Construction of nitrogen-containing 9-membered ring epoxy vinyl ethers via gold(I)-catalyzed intramolecular cyclization reactions of acyclic 5-aza-2,3-epoxy-7-yn-1-ols

Hsin Hui Lin, Yi Ju Chen, Kuan Yu Liao, Ming Chang P. Yeh

Research output: Contribution to journalArticle

Abstract

A series of substituted nitrogen-containing 9-membered epoxy vinyl ethers has been constructed from easily available 5-aza-2,3-epoxy-7-yn-1-ols. Attack of the hydroxyl group onto the gold(I)-activated alkyne gave the postulated 9-membered allylic vinyl ether gold intermediate which underwent protodeauration affording the 9-membered epoxy vinyl ethers.

Original languageEnglish
Pages (from-to)1281-1288
Number of pages8
JournalJournal of the Chinese Chemical Society
Volume61
Issue number12
DOIs
Publication statusPublished - 2014 Jul 25

Fingerprint

Cyclization
Gold
Nitrogen
Alkynes
Hydroxyl Radical
vinyl ether

Keywords

  • Alcohol
  • Alkyne
  • Claisen rearrangement
  • Epoxy
  • Gold
  • Vinyl ether

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Construction of nitrogen-containing 9-membered ring epoxy vinyl ethers via gold(I)-catalyzed intramolecular cyclization reactions of acyclic 5-aza-2,3-epoxy-7-yn-1-ols",
abstract = "A series of substituted nitrogen-containing 9-membered epoxy vinyl ethers has been constructed from easily available 5-aza-2,3-epoxy-7-yn-1-ols. Attack of the hydroxyl group onto the gold(I)-activated alkyne gave the postulated 9-membered allylic vinyl ether gold intermediate which underwent protodeauration affording the 9-membered epoxy vinyl ethers.",
keywords = "Alcohol, Alkyne, Claisen rearrangement, Epoxy, Gold, Vinyl ether",
author = "Lin, {Hsin Hui} and Chen, {Yi Ju} and Liao, {Kuan Yu} and Yeh, {Ming Chang P.}",
year = "2014",
month = "7",
day = "25",
doi = "10.1002/jccs.201400121",
language = "English",
volume = "61",
pages = "1281--1288",
journal = "Journal of the Chinese Chemical Society",
issn = "0009-4536",
publisher = "Chinese Chemical Society",
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T1 - Construction of nitrogen-containing 9-membered ring epoxy vinyl ethers via gold(I)-catalyzed intramolecular cyclization reactions of acyclic 5-aza-2,3-epoxy-7-yn-1-ols

AU - Lin, Hsin Hui

AU - Chen, Yi Ju

AU - Liao, Kuan Yu

AU - Yeh, Ming Chang P.

PY - 2014/7/25

Y1 - 2014/7/25

N2 - A series of substituted nitrogen-containing 9-membered epoxy vinyl ethers has been constructed from easily available 5-aza-2,3-epoxy-7-yn-1-ols. Attack of the hydroxyl group onto the gold(I)-activated alkyne gave the postulated 9-membered allylic vinyl ether gold intermediate which underwent protodeauration affording the 9-membered epoxy vinyl ethers.

AB - A series of substituted nitrogen-containing 9-membered epoxy vinyl ethers has been constructed from easily available 5-aza-2,3-epoxy-7-yn-1-ols. Attack of the hydroxyl group onto the gold(I)-activated alkyne gave the postulated 9-membered allylic vinyl ether gold intermediate which underwent protodeauration affording the 9-membered epoxy vinyl ethers.

KW - Alcohol

KW - Alkyne

KW - Claisen rearrangement

KW - Epoxy

KW - Gold

KW - Vinyl ether

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