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Updated: Jul 7, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Facile and highly stereoselective one-pot synthesis of either (E)- or (Z)-nitro alkenes
Stefania Fioravanti1, Lucio Pellacani, Paolo A Tardella
1Dipartimento di Chimica, Università degli Studi La Sapienza, P.le Aldo Moro 2, I-00185 Roma, Italy.
Abstract:
Aliphatic aldehydes were reacted with nitro alkanes in the presence of catalytic amounts of piperidine over 4 A molecular sieves. Simply by changing reaction conditions (solvent and temperature) it is possible to control the stereochemical outcome of the reactions, obtaining pure (E)- and (Z)-nitro alkenes in high to excellent yields. The role of molecular sieves on the stereochemical control seems crucial in addition to that of piperidine, especially for the synthesis of the Z isomer.
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