Synthesis of 2,5-disubstituted dihydrofuran-3(2 H)-ones via [2,3]-sigmatropic rearrangement of oxonium ylides generated from α-oxo gold carbenes

Miyeon Han; Joohee Bae; Juhee Choi; Jinsung Tae

doi:10.1055/s-0033-1339662

Synthesis of 2,5-disubstituted dihydrofuran-3(2 H)-ones via [2,3]-sigmatropic rearrangement of oxonium ylides generated from α-oxo gold carbenes

Miyeon Han, Joohee Bae, Juhee Choi, Jinsung Tae

Department of Chemistry

Research output: Contribution to journal › Article

7 Citations (Scopus)

Abstract

Novel [2,3]-sigmatropic rearrangements of oxonium ylides generated from α-oxo gold carbenes were discovered. An efficient synthetic method of 2,5-disubstituted dihydrofuran-3(2H)-ones via gold-catalyzed intermolecular oxidation of the allyl homopropargyl ethers with N-oxide was developed. And the synthetic utility of the current method has been proved by concise formal synthesis of (±)-kumausallene.

Original language	English
Article number	ST-2013-U0608-L
Pages (from-to)	2077-2080
Number of pages	4
Journal	Synlett
Volume	24
Issue number	16
DOIs	https://doi.org/10.1055/s-0033-1339662
Publication status	Published - 2013

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1055/s-0033-1339662

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abstract = "Novel [2,3]-sigmatropic rearrangements of oxonium ylides generated from α-oxo gold carbenes were discovered. An efficient synthetic method of 2,5-disubstituted dihydrofuran-3(2H)-ones via gold-catalyzed intermolecular oxidation of the allyl homopropargyl ethers with N-oxide was developed. And the synthetic utility of the current method has been proved by concise formal synthesis of (±)-kumausallene.",

author = "Miyeon Han and Joohee Bae and Juhee Choi and Jinsung Tae",

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AU - Han, Miyeon

AU - Bae, Joohee

AU - Choi, Juhee

AU - Tae, Jinsung

PY - 2013

Y1 - 2013

N2 - Novel [2,3]-sigmatropic rearrangements of oxonium ylides generated from α-oxo gold carbenes were discovered. An efficient synthetic method of 2,5-disubstituted dihydrofuran-3(2H)-ones via gold-catalyzed intermolecular oxidation of the allyl homopropargyl ethers with N-oxide was developed. And the synthetic utility of the current method has been proved by concise formal synthesis of (±)-kumausallene.

AB - Novel [2,3]-sigmatropic rearrangements of oxonium ylides generated from α-oxo gold carbenes were discovered. An efficient synthetic method of 2,5-disubstituted dihydrofuran-3(2H)-ones via gold-catalyzed intermolecular oxidation of the allyl homopropargyl ethers with N-oxide was developed. And the synthetic utility of the current method has been proved by concise formal synthesis of (±)-kumausallene.

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