Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine

A new highly efficient three-component reaction of alkyl acrylate, aldehyde and dialkyl malonate using ethyl diphenylphosphine as organocatalyst has been described. Various highly functional compounds bearing hydroxyl groups and the ester functions can be easily prepared in moderate to good yields a...

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Autores principales: Jang, Yeong-Jiunn, Syu, Siang-En, Jhang, Yi-Wun, Lee, Yu-Ting, Lee, Chia-Jui, Chen, Ko-Wei, Das, Utpal, Lin, Wenwei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268679/
https://www.ncbi.nlm.nih.gov/pubmed/22446986
http://dx.doi.org/10.3390/molecules17032529
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author Jang, Yeong-Jiunn
Syu, Siang-En
Jhang, Yi-Wun
Lee, Yu-Ting
Lee, Chia-Jui
Chen, Ko-Wei
Das, Utpal
Lin, Wenwei
author_facet Jang, Yeong-Jiunn
Syu, Siang-En
Jhang, Yi-Wun
Lee, Yu-Ting
Lee, Chia-Jui
Chen, Ko-Wei
Das, Utpal
Lin, Wenwei
author_sort Jang, Yeong-Jiunn
collection PubMed
description A new highly efficient three-component reaction of alkyl acrylate, aldehyde and dialkyl malonate using ethyl diphenylphosphine as organocatalyst has been described. Various highly functional compounds bearing hydroxyl groups and the ester functions can be easily prepared in moderate to good yields according to our one-step procedure. The reactions are believed to proceed via Morita-Baylis-Hillman reactions of alkyl acrylate and aldehydes, followed by the Michael addition reactions of dialkyl malonates. Our reactions indicated that the intermediate species formed in the phosphine-catalyzed MBH reaction are an effective organic base to catalyze the Michael addition reactions of dialkyl malonates to the preformed MBH adducts.
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spelling pubmed-62686792018-12-20 Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine Jang, Yeong-Jiunn Syu, Siang-En Jhang, Yi-Wun Lee, Yu-Ting Lee, Chia-Jui Chen, Ko-Wei Das, Utpal Lin, Wenwei Molecules Article A new highly efficient three-component reaction of alkyl acrylate, aldehyde and dialkyl malonate using ethyl diphenylphosphine as organocatalyst has been described. Various highly functional compounds bearing hydroxyl groups and the ester functions can be easily prepared in moderate to good yields according to our one-step procedure. The reactions are believed to proceed via Morita-Baylis-Hillman reactions of alkyl acrylate and aldehydes, followed by the Michael addition reactions of dialkyl malonates. Our reactions indicated that the intermediate species formed in the phosphine-catalyzed MBH reaction are an effective organic base to catalyze the Michael addition reactions of dialkyl malonates to the preformed MBH adducts. MDPI 2012-03-02 /pmc/articles/PMC6268679/ /pubmed/22446986 http://dx.doi.org/10.3390/molecules17032529 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Jang, Yeong-Jiunn
Syu, Siang-En
Jhang, Yi-Wun
Lee, Yu-Ting
Lee, Chia-Jui
Chen, Ko-Wei
Das, Utpal
Lin, Wenwei
Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine
title Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine
title_full Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine
title_fullStr Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine
title_full_unstemmed Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine
title_short Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine
title_sort tandem three-component reactions of aldehyde, alkyl acrylate, and dialkylmalonate catalyzed by ethyl diphenylphosphine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268679/
https://www.ncbi.nlm.nih.gov/pubmed/22446986
http://dx.doi.org/10.3390/molecules17032529
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