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^*

^*Corresponding author for this work

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)

Access to Document

10.1002/jccs.201400121

Cite this

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 et al.

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",

author = "Lin, {Hsin Hui} and Chen, {Yi Ju} and Liao, {Kuan Yu} and Yeh, {Ming Chang P.}",

note = "Publisher Copyright: {\textcopyright} 2014 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2014",

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day = "25",

doi = "10.1002/jccs.201400121",

language = "English",

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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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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

Access to Document

Other files and links

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CCDC 970660: Experimental Crystal Structure Determination

CCDC 970662: Experimental Crystal Structure Determination

CCDC 970842: Experimental Crystal Structure Determination

Cite this

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

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 970660: Experimental Crystal Structure Determination

CCDC 970662: Experimental Crystal Structure Determination

CCDC 970842: Experimental Crystal Structure Determination

Cite this