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, Università 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