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Article

Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers

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Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas, Astrofísico Francisco Sánchez 3, 38206 La Laguna, Spain
2
Doctoral and Postgraduate School, Universidad de La Laguna, Apartado Postal 456, 38200 La Laguna, Spain
*
Authors to whom correspondence should be addressed.
Academic Editors: Ana Maria Gomez Neo and Carlos Fernández Marcos
Molecules 2021, 26(14), 4120; https://doi.org/10.3390/molecules26144120
Received: 21 June 2021 / Revised: 30 June 2021 / Accepted: 2 July 2021 / Published: 6 July 2021
(This article belongs to the Special Issue New Approach in Multicomponent Reactions)
A novel organocatalytic multicomponent cyanovinylation of aldehydes was designed for the synthesis of conjugated cyanomethyl vinyl ethers. The reaction was implemented for the synthesis of a 3-substituted 3-(cyanomethoxy)acrylates, using aldehydes as substrates, acetone cyanohydrin as the cyanide anion source, and methyl propiolate as the source of the vinyl component. The multicomponent reaction is catalyzed by N-methyl morpholine (2.5 mol%) to deliver the 3-(cyanomethoxy)acrylates in excellent yields and with preponderance of the E-isomer. The multicomponent reaction manifold is highly tolerant to the structure and composition of the aldehyde (aliphatic, aromatic, heteroaromatics), and it is instrumentally simple (one batch, open atmospheres), economic (2.5 mol% catalyst, stoichiometric reagents), environmentally friendly (no toxic waste), and sustainable (easy scalability). View Full-Text
Keywords: cyanomethyl vinyl ethers; 3-(cyanomethoxy)acrylates; multicomponent; cyanohydrin; cyanovinylation; organocatalysis; tertiary amine; N-methyl morpholine cyanomethyl vinyl ethers; 3-(cyanomethoxy)acrylates; multicomponent; cyanohydrin; cyanovinylation; organocatalysis; tertiary amine; N-methyl morpholine
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MDPI and ACS Style

Delgado-Hernández, S.; García-Tellado, F.; Tejedor, D. Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers. Molecules 2021, 26, 4120. https://doi.org/10.3390/molecules26144120

AMA Style

Delgado-Hernández S, García-Tellado F, Tejedor D. Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers. Molecules. 2021; 26(14):4120. https://doi.org/10.3390/molecules26144120

Chicago/Turabian Style

Delgado-Hernández, Samuel, Fernando García-Tellado, and David Tejedor. 2021. "Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers" Molecules 26, no. 14: 4120. https://doi.org/10.3390/molecules26144120

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