tandem three-component reactions of aldehyde, alkyl acrylate, and dialkylmalonate catalyzed by ethyl diphenylphosphine串联三分量的醛的反应、烷基丙烯酸酯,乙基diphenylphosphine dialkylmalonate催化.pdfVIP

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tandem three-component reactions of aldehyde, alkyl acrylate, and dialkylmalonate catalyzed by ethyl diphenylphosphine串联三分量的醛的反应、烷基丙烯酸酯,乙基diphenylphosphine dialkylmalonate催化.pdf

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tandem three-component reactions of aldehyde, alkyl acrylate, and dialkylmalonate catalyzed by ethyl diphenylphosphine串联三分量的醛的反应、烷基丙烯酸酯,乙基diphenylphosphine dialkylmalonate催化

Molecules 2012, 17, 2529-2541; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules 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 * Department of Chemistry, National Taiwan Normal University No. 88, Section 4, Tingchow Road, Taipei 11677, Taiwan * Author to whom correspondence should be addressed; E-Mail: wenweilin@.tw; Tel.: +886-(0)2-2932-4249. Received: 19 December 2011; in revised form: 9 February 2012 / Accepted: 17 February 2012 / Published: 2 March 2012 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; che