Next Article in Journal
The Artemisia L. Genus: A Review of Bioactive Essential Oils
Next Article in Special Issue
4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen
Previous Article in Journal
Effects of Different Extraction Methods and Conditions on the Phenolic Composition of Mate Tea Extracts
Previous Article in Special Issue
Contribution of Cation-π Interactions in Iminium Catalysis
Molecules 2012, 17(3), 2529-2541; doi:10.3390/molecules17032529
Article

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

, , , , , ,  and *
Received: 19 December 2011; in revised form: 9 February 2012 / Accepted: 17 February 2012 / Published: 2 March 2012
(This article belongs to the Special Issue Organocatalysis)
Download PDF [255 KB, uploaded 18 June 2014]
Abstract: 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.
Keywords: multicomponent reaction; Morita-Baylis-Hillman; chemoselectivity; Michael addition; aldehyde multicomponent reaction; Morita-Baylis-Hillman; chemoselectivity; Michael addition; aldehyde
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

Jang, Y.-J.; Syu, S.-E.; Jhang, Y.-W.; Lee, Y.-T.; Lee, C.-J.; Chen, K.-W.; Das, U.; Lin, W. Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine. Molecules 2012, 17, 2529-2541.

AMA Style

Jang Y-J, Syu S-E, Jhang Y-W, Lee Y-T, Lee C-J, Chen K-W, Das U, Lin W. Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine. Molecules. 2012; 17(3):2529-2541.

Chicago/Turabian Style

Jang, Yeong-Jiunn; Syu, Siang-En; Jhang, Yi-Wun; Lee, Yu-Ting; Lee, Chia-Jui; Chen, Ko-Wei; Das, Utpal; Lin, Wenwei. 2012. "Tandem Three-Component Reactions of Aldehyde, Alkyl Acrylate, and Dialkylmalonate Catalyzed by Ethyl Diphenylphosphine." Molecules 17, no. 3: 2529-2541.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert