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, Wen-Wei Lin

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)5943-5946
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number45
DOIs
Publication statusPublished - 2010 Nov 10

Fingerprint

Aldehydes
Amides
Acrylates
acrylic acid
phthalimide

Keywords

  • Aldehyde
  • Chemoselectivity
  • Michael addition
  • Morita-Baylis-Hillman
  • Multicomponent reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst. / Syu, Siang En; Wang, De Wei; Chen, Pei Yi; Hung, Yi Ting; Jhang, Yi Wun; Kao, Tzu Ting; Lee, Yu Ting; Lin, Wen-Wei.

In: Tetrahedron Letters, Vol. 51, No. 45, 10.11.2010, p. 5943-5946.

Research output: Contribution to journalArticle

Syu, Siang En ; Wang, De Wei ; Chen, Pei Yi ; Hung, Yi Ting ; Jhang, Yi Wun ; Kao, Tzu Ting ; Lee, Yu Ting ; Lin, Wen-Wei. / Tandem three-component reaction of aldehyde, alkyl acrylate, and amide using ethyl diphenylphosphine as organocatalyst. In: Tetrahedron Letters. 2010 ; Vol. 51, No. 45. pp. 5943-5946.
@article{d275bd5e76db4299b5c723c1d761eda5,
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 Wen-Wei Lin",
year = "2010",
month = "11",
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, Wen-Wei

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

VL - 51

SP - 5943

EP - 5946

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 45

ER -