Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst

Siang En Syu; De Wei Wang; Pei Yi Chen; Yi Ting Hung; Yi Wun Jhang; Tzu Ting Kao; Yu Ting Lee; Wenwei Lin

doi:10.1016/j.tetlet.2010.09.020

Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst

Siang En Syu
, De Wei Wang
, Pei Yi Chen
, Yi Ting Hung
, Yi Wun Jhang
, Tzu Ting Kao
, Yu Ting Lee
, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

11 Citations (Scopus)

Abstract

It is the first time that a chemoselective EtPPh₂-catalyzed three-component reaction of aromatic aldehyde, alkyl acrylate, and phthalimide or methyl toluenesulfonamide has been achieved. A variety of highly functional adducts can be generated efficiently in one step within 1-72 h in 38-93% yields. The reaction mechanism is proposed to undergo Morita-Baylis-Hillman reactions of aryl-substituted aldehydes and alkyl acrylates followed by Michael additions of amides. Our studies indicated that, in combination of EtPPh₂, alkyl acrylate also catalyzed this process.

Original language	English
Pages (from-to)	5943-5946
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	45
DOIs	https://doi.org/10.1016/j.tetlet.2010.09.020
Publication status	Published - 2010 Nov 10

Keywords

Aldehyde
Chemoselectivity
Michael addition
Morita-Baylis-Hillman
Multicomponent reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.09.020

Cite this

@article{a921a61894b04f068d65499d4dae0136,

title = "Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst",

abstract = "It is the first time that a chemoselective EtPPh2-catalyzed three-component reaction of aromatic aldehyde, alkyl acrylate, and phthalimide or methyl toluenesulfonamide has been achieved. A variety of highly functional adducts can be generated efficiently in one step within 1-72 h in 38-93\% yields. The reaction mechanism is proposed to undergo Morita-Baylis-Hillman reactions of aryl-substituted aldehydes and alkyl acrylates followed by Michael additions of amides. Our studies indicated that, in combination of EtPPh2, alkyl acrylate also catalyzed this process.",

keywords = "Aldehyde, Chemoselectivity, Michael addition, Morita-Baylis-Hillman, Multicomponent reaction",

author = "Syu, \{Siang En\} and Wang, \{De Wei\} and Chen, \{Pei Yi\} and Hung, \{Yi Ting\} and Jhang, \{Yi Wun\} and Kao, \{Tzu Ting\} and Lee, \{Yu Ting\} and Wenwei Lin",

note = "Funding Information: We thank the National Science Council of the Republic of China (NSC Grant No. 97-2113-M-003-003-MY2 ) and National Taiwan Normal University ( 99031019 ) for financial support. ",

year = "2010",

month = nov,

day = "10",

doi = "10.1016/j.tetlet.2010.09.020",

language = "English",

volume = "51",

pages = "5943--5946",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "45",

}

TY - JOUR

T1 - Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst

AU - Syu, Siang En

AU - Wang, De Wei

AU - Chen, Pei Yi

AU - Hung, Yi Ting

AU - Jhang, Yi Wun

AU - Kao, Tzu Ting

AU - Lee, Yu Ting

AU - Lin, Wenwei

N1 - Funding Information: We thank the National Science Council of the Republic of China (NSC Grant No. 97-2113-M-003-003-MY2 ) and National Taiwan Normal University ( 99031019 ) for financial support.

PY - 2010/11/10

Y1 - 2010/11/10

N2 - It is the first time that a chemoselective EtPPh2-catalyzed three-component reaction of aromatic aldehyde, alkyl acrylate, and phthalimide or methyl toluenesulfonamide has been achieved. A variety of highly functional adducts can be generated efficiently in one step within 1-72 h in 38-93% yields. The reaction mechanism is proposed to undergo Morita-Baylis-Hillman reactions of aryl-substituted aldehydes and alkyl acrylates followed by Michael additions of amides. Our studies indicated that, in combination of EtPPh2, alkyl acrylate also catalyzed this process.

AB - It is the first time that a chemoselective EtPPh2-catalyzed three-component reaction of aromatic aldehyde, alkyl acrylate, and phthalimide or methyl toluenesulfonamide has been achieved. A variety of highly functional adducts can be generated efficiently in one step within 1-72 h in 38-93% yields. The reaction mechanism is proposed to undergo Morita-Baylis-Hillman reactions of aryl-substituted aldehydes and alkyl acrylates followed by Michael additions of amides. Our studies indicated that, in combination of EtPPh2, alkyl acrylate also catalyzed this process.

KW - Aldehyde

KW - Chemoselectivity

KW - Michael addition

KW - Morita-Baylis-Hillman

KW - Multicomponent reaction

UR - https://www.scopus.com/pages/publications/77957800141

UR - https://www.scopus.com/pages/publications/77957800141#tab=citedBy

U2 - 10.1016/j.tetlet.2010.09.020

DO - 10.1016/j.tetlet.2010.09.020

M3 - Article

AN - SCOPUS:77957800141

SN - 0040-4039

VL - 51

SP - 5943

EP - 5946

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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CCDC 748316: Experimental Crystal Structure Determination

CCDC 744772: Experimental Crystal Structure Determination

CCDC 744771: Experimental Crystal Structure Determination

Cite this

Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 748316: Experimental Crystal Structure Determination

CCDC 744772: Experimental Crystal Structure Determination

CCDC 744771: Experimental Crystal Structure Determination

Cite this