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.pellacani
uniroma1.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
