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 › peer-review

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

Keywords

Cyclopropane
Multi-functional alkene
Phosphorus ylide
Pyridazinone
Wittig reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides",

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.",

keywords = "Cyclopropane, Multi-functional alkene, Phosphorus ylide, Pyridazinone, Wittig reaction",

author = "Tsai, {Yi Ling} and Syu, {Siang En} and Yang, {Shu Mei} and Utpal Das and Fan, {Yu Shiou} and Lee, {Chia Jui} and Wenwei Lin",

year = "2014",

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day = "26",

doi = "10.1016/j.tet.2014.06.015",

language = "English",

volume = "70",

pages = "5038--5045",

journal = "Tetrahedron",

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T1 - Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides

AU - Tsai, Yi Ling

AU - Syu, Siang En

AU - Yang, Shu Mei

AU - Das, Utpal

AU - Fan, Yu Shiou

AU - Lee, Chia Jui

AU - Lin, Wenwei

PY - 2014/8/26

Y1 - 2014/8/26

N2 - 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.

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.

KW - Cyclopropane

KW - Multi-functional alkene

KW - Phosphorus ylide

KW - Pyridazinone

KW - Wittig reaction

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DO - 10.1016/j.tet.2014.06.015

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SP - 5038

EP - 5045

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 34

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