Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides

Yi Ling Tsai, Siang En Syu, Shu Mei Yang, Utpal Das, Yu Shiou Fan, Chia Jui Lee, Wenwei Lin

Research output: Contribution to journal › Article

10 Citations (Scopus)

Abstract

A Bu3P-mediated mild and efficient synthesis of multi-functional alkenes has been described starting from substituted acrylate with aldehydes. In situ generated zwitterionic intermediates underwent proton-exchange to afford ylide intermediates, which were trapped by corresponding aldehydes providing the products in up to 92% yield with complete E-stereoselectivity. Further derivatization of the products was performed to furnish functional pyridazinones.

Original languageEnglish
Pages (from-to)5038-5045
Number of pages8
JournalTetrahedron
Volume70
Issue number34
DOIs
Publication statusPublished - 2014 Aug 26

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Alkenes
Aldehydes
Phosphorus
Stereoselectivity
Protons
acrylic acid

Keywords

  • Cyclopropane
  • Multi-functional alkene
  • Phosphorus ylide
  • Pyridazinone
  • Wittig reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides. / Tsai, Yi Ling; Syu, Siang En; Yang, Shu Mei; Das, Utpal; Fan, Yu Shiou; Lee, Chia Jui; Lin, Wenwei.

In: Tetrahedron, Vol. 70, No. 34, 26.08.2014, p. 5038-5045.

Research output: Contribution to journal › Article

Tsai, YL, Syu, SE, Yang, SM, Das, U, Fan, YS, Lee, CJ & Lin, W 2014, 'Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides', Tetrahedron, vol. 70, no. 34, pp. 5038-5045. https://doi.org/10.1016/j.tet.2014.06.015
Tsai YL, Syu SE, Yang SM, Das U, Fan YS, Lee CJ et al. Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides. Tetrahedron. 2014 Aug 26;70(34):5038-5045. https://doi.org/10.1016/j.tet.2014.06.015
Tsai, Yi Ling ; Syu, Siang En ; Yang, Shu Mei ; Das, Utpal ; Fan, Yu Shiou ; Lee, Chia Jui ; Lin, Wenwei. / Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides. In: Tetrahedron. 2014 ; Vol. 70, No. 34. pp. 5038-5045.
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AU - Das, Utpal

AU - Fan, Yu Shiou

AU - Lee, Chia Jui

AU - Lin, Wenwei

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