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

Department of Chemistry

Research output: Contribution to journal › Article

9 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

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Keywords

Aldehyde
Chemoselectivity
Michael addition
Morita-Baylis-Hillman
Multicomponent reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Syu, S. E., Wang, D. W., Chen, P. Y., Hung, Y. T., Jhang, Y. W., Kao, T. T., Lee, Y. T., & Lin, W. (2010). Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst. Tetrahedron Letters, 51(45), 5943-5946. https://doi.org/10.1016/j.tetlet.2010.09.020

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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.",

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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

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

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Access to Document

10.1016/j.tetlet.2010.09.020