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

Research output: Contribution to journalArticle

17 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 languageEnglish
Pages (from-to)5156-5161
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number31
DOIs
Publication statusPublished - 2013 Aug 21

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Furans
furans
Ketones
Discrete Fourier transforms
Phosphorus
Chlorides
Electrons
Derivatives
Acids
synthesis
ketones
phosphorus
chlorides
acids
electrons

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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 journalArticle

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