Organic letters

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

S Fioravanti, L Pellacani, PA Tardella…

Index: Fioravanti, Stefania; Pellacani, Lucio; Tardella, Paolo A.; Vergari, Maria Cecilia Organic Letters, 2008 , vol. 10, # 7 p. 1449 - 1451

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Citation Number: 52

Abstract

Aliphatic aldehydes were reacted with nitro alkanes in the presence of catalytic amounts of piperidine over 4 Å 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 ...