Chemoselective synthesis of tetrasubstituted furans via intramolecular Wittig reactions: Mechanism and theoretical analysis

Yu Ting Lee; Yen Te Lee; Chia Jui Lee; Chia Ning Sheu; Bo Yu Lin; Jeng Han Wang; Wenwei Lin

doi:10.1039/c3ob40858b

Chemoselective synthesis of tetrasubstituted furans via intramolecular Wittig reactions: Mechanism and theoretical analysis

Yu Ting Lee, Yen Te Lee, Chia Jui Lee, Chia Ning Sheu, Bo Yu Lin, Jeng Han Wang, Wenwei Lin

Department of Chemistry

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

21 Citations (Scopus)

Abstract

An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu₃P in the presence of Et₃N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus ylides in the intramolecular Wittig reactions, and their mechanisms were also investigated by DFT calculations.

Original language	English
Pages (from-to)	5156-5161
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	31
DOIs	https://doi.org/10.1039/c3ob40858b
Publication status	Published - 2013 Aug 21

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Chemoselective synthesis of tetrasubstituted furans via intramolecular Wittig reactions : Mechanism and theoretical analysis. / Lee, Yu Ting; Lee, Yen Te; Lee, Chia Jui; Sheu, Chia Ning; Lin, Bo Yu; Wang, Jeng Han ; Lin, Wenwei.

In: Organic and Biomolecular Chemistry, Vol. 11, No. 31, 21.08.2013, p. 5156-5161.

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

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abstract = "An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus ylides in the intramolecular Wittig reactions, and their mechanisms were also investigated by DFT calculations.",

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AU - Lee, Yen Te

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AU - Sheu, Chia Ning

AU - Lin, Bo Yu

AU - Wang, Jeng Han

AU - Lin, Wenwei

PY - 2013/8/21

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N2 - An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus ylides in the intramolecular Wittig reactions, and their mechanisms were also investigated by DFT calculations.

AB - An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus ylides in the intramolecular Wittig reactions, and their mechanisms were also investigated by DFT calculations.

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Chemoselective synthesis of tetrasubstituted furans via intramolecular Wittig reactions: Mechanism and theoretical analysis

Abstract

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