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

doi:10.1002/jccs.201400121

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	1281-1288
Number of pages	8
Journal	Journal of the Chinese Chemical Society
Volume	61
Issue number	12
DOIs	https://doi.org/10.1002/jccs.201400121
Publication status	Published - 2014 Jul 25

Keywords

Alcohol
Alkyne
Claisen rearrangement
Epoxy
Gold
Vinyl ether

ASJC Scopus subject areas

Chemistry(all)

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10.1002/jccs.201400121

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

In: Journal of the Chinese Chemical Society, Vol. 61, No. 12, 25.07.2014, p. 1281-1288.

Research output: Contribution to journal › Article › peer-review

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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",

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AU - Liao, Kuan Yu

AU - Yeh, Ming Chang P.

PY - 2014/7/25

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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.

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KW - Claisen rearrangement

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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

Keywords

ASJC Scopus subject areas

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