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

doi:10.1016/j.tet.2014.06.015

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

Department of Chemistry

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 language	English
Pages (from-to)	5038-5045
Number of pages	8
Journal	Tetrahedron
Volume	70
Issue number	34
DOIs	https://doi.org/10.1016/j.tet.2014.06.015
Publication status	Published - 2014 Aug 26

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Keywords

Cyclopropane
Multi-functional alkene
Phosphorus ylide
Pyridazinone
Wittig reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Tsai, Y. L., Syu, S. E., Yang, S. M., Das, U., Fan, Y. S., Lee, C. J., & Lin, W. (2014). Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides. Tetrahedron, 70(34), 5038-5045. https://doi.org/10.1016/j.tet.2014.06.015

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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.",

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AU - Das, Utpal

AU - Fan, Yu Shiou

AU - Lee, Chia Jui

AU - Lin, Wenwei

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AB - 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.

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KW - Multi-functional alkene

KW - Phosphorus ylide

KW - Pyridazinone

KW - Wittig reaction

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10.1016/j.tet.2014.06.015