Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers |
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Authors: | Samuel Delgado-Hernndez Fernando García-Tellado David Tejedor |
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Institution: | 1.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 |
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Abstract: | 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). |
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Keywords: | cyanomethyl vinyl ethers 3-(cyanomethoxy)acrylates multicomponent cyanohydrin cyanovinylation organocatalysis tertiary amine N-methyl morpholine |
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