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Facile and Highly Stereoselective One-Pot Synthesis of Either (E)- or (Z)-Nitro Alkenes

Stefania Fioravanti, Lucio Pellacani,* Paolo A. Tardella and Maria Cecilia Vergari

*Dipartimento di Chimica, UniversitÓ degli Studi La Sapienza, P.le Aldo Moro 2, I-00185 Roma, Italy, Email: lucio.pellacaniuniroma1.it

S. Fioravanti, L. Pellacani, P. A. Tardella, M. C. Vergari, Org. Lett., 2008, 10, 1449-1451.

DOI: 10.1021/ol800224k


Abstract

By changing reaction conditions (solvent and temperature), it is possible to control the stereochemical outcome of the condensation of aliphatic aldehydes with nitro alkanes 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 for the synthesis of the Z isomer.

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Key Words

Knoevenagel Condensation, Nitroalkenes


ID: J54-Y2008-0950