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 - http://www.scopus.com/inward/record.url?scp=77957800141&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77957800141&partnerID=8YFLogxK

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 753480: Experimental Crystal Structure Determination

CCDC 752968: 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 753480: Experimental Crystal Structure Determination

CCDC 752968: Experimental Crystal Structure Determination

Cite this