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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

12 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	5038-5045
頁數	8
期刊	Tetrahedron
卷	70
發行號	34
DOIs	https://doi.org/10.1016/j.tet.2014.06.015
出版狀態	已發佈 - 2014 8月 26

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

存取文件

10.1016/j.tet.2014.06.015

其它文件與鏈接

CCDC 986508: Experimental Crystal Structure Determination
Tsai, Y.-L. (Creator), Syu, S.-E. (Creator), Yang, S.-M. (Creator), Das, U. (Creator), Fan, Y.-S. (Creator), Lee, C.-J. (Creator) & Lin, W. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc123jvk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc123jvk&sid=DataCite
資料集: Dataset
CCDC 986510: Experimental Crystal Structure Determination
Tsai, Y.-L. (Creator), Syu, S.-E. (Creator), Yang, S.-M. (Creator), Das, U. (Creator), Fan, Y.-S. (Creator), Lee, C.-J. (Creator) & Lin, W. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc123jxm, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc123jxm&sid=DataCite
資料集: Dataset
CCDC 986509: Experimental Crystal Structure Determination
Tsai, Y.-L. (Creator), Syu, S.-E. (Creator), Yang, S.-M. (Creator), Das, U. (Creator), Fan, Y.-S. (Creator), Lee, C.-J. (Creator) & Lin, W. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc123jwl, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc123jwl&sid=DataCite
資料集: Dataset

引用此

@article{9e24ab32dedc4c37afea2da566204558,

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",

note = "Funding Information: The authors thank the Ministry of Science and Technology of the R.O.C., Taiwan ( NSC 101-2113-M-003-001-MY3 ) and National Taiwan Normal University ( NTNU 100-D-06 ) for financial support. ",

year = "2014",

month = aug,

day = "26",

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

language = "English",

volume = "70",

pages = "5038--5045",

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number = "34",

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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

N1 - Funding Information: The authors thank the Ministry of Science and Technology of the R.O.C., Taiwan ( NSC 101-2113-M-003-001-MY3 ) and National Taiwan Normal University ( NTNU 100-D-06 ) for financial support.

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

UR - http://www.scopus.com/inward/record.url?scp=84903385832&partnerID=8YFLogxK

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U2 - 10.1016/j.tet.2014.06.015

DO - 10.1016/j.tet.2014.06.015

M3 - Article

AN - SCOPUS:84903385832

SN - 0040-4020

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SP - 5038

EP - 5045

JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 986508: Experimental Crystal Structure Determination

CCDC 986510: Experimental Crystal Structure Determination

CCDC 986509: Experimental Crystal Structure Determination

引用此