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

Yeong-Jiunn Jang, Siang-En Syu, Yi-Wun Jhang, Yu-Ting Lee, Chia-Jui Lee, Ko-Wei Chen, Utpal Das and Wenwei Lin* email
Department of Chemistry, National Taiwan Normal University No. 88, Section 4, Tingchow Road, Taipei 11677, Taiwan
* Author to whom correspondence should be addressed.
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)
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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

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Cite This Article

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.

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