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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Published inMolecules (Basel, Switzerland) Vol. 17; no. 3; pp. 2529 - 2541
Main Authors Jang, Yeong-Jiunn, Syu, Siang-En, Jhang, Yi-Wun, Lee, Yu-Ting, Lee, Chia-Jui, Chen, Ko-Wei, Das, Utpal, Lin, Wenwei
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 02.03.2012
MDPI
Subjects
Acrylates - chemistry
aldehyde
Aldehydes - chemistry
Carbon
Catalysis
chemoselectivity
Malonates - chemistry
Michael addition
Molecular Structure
Morita-Baylis-Hillman
multicomponent reaction
Phosphines - chemistry
Solvents
Stereoisomerism
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Summary: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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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules17032529