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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

14 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

Access to Document

10.1016/j.tet.2014.06.015

Cite this

@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",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "34",

}

TY - JOUR

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 - https://www.scopus.com/pages/publications/84903385832

UR - https://www.scopus.com/pages/publications/84903385832#tab=citedBy

U2 - 10.1016/j.tet.2014.06.015

DO - 10.1016/j.tet.2014.06.015

M3 - Article

AN - SCOPUS:84903385832

SN - 0040-4020

VL - 70

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 986510: Experimental Crystal Structure Determination

CCDC 986508: Experimental Crystal Structure Determination

CCDC 986509: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 986510: Experimental Crystal Structure Determination

CCDC 986508: Experimental Crystal Structure Determination

CCDC 986509: Experimental Crystal Structure Determination

Cite this