A Practical,efficient, and atom economic alternative to the Wittig and Horner–Wadsworth–Emmons reactions for the synthesis of (E)-α,β-unsaturated esters from aldehydes |
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Institution: | 1. Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany;2. Lanxess Deutschland GmbH, Building Q-18, 51369 Leverkusen Germany |
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Abstract: | We describe a highly efficient new methodology for the synthesis of (E)-α,β-unsaturated esters from aldehydes. In our DMAP-catalyzed reaction, both aromatic as well as aliphatic aldehydes furnish the desired products highly regio- and stereoselectively if treated with commercially available or synthetically easily accessible malonic acid half ester. A large scale application in the synthesis of p-methoxycinnamates, which are of use as sunscreen ingredients, is described. |
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