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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 (free Supporting Information)


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