Aliphatic aldehydes were reacted with nitro alkanes in the presence of catalytic amounts of piperidine over 4 angstrom 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 synthesis of the Z isomer.
Facile and highly stereoselective one-pot synthesis of either (E)- or (Z)-nitro alkenes / Fioravanti, Stefania; Pellacani, Lucio; Tardella, Paolo Antonio; Vergari, MARIA CECILIA. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 10:7(2008), pp. 1449-1451. [10.1021/ol800224k]
Facile and highly stereoselective one-pot synthesis of either (E)- or (Z)-nitro alkenes
FIORAVANTI, Stefania;PELLACANI, Lucio;TARDELLA, Paolo Antonio;VERGARI, MARIA CECILIA
2008
Abstract
Aliphatic aldehydes were reacted with nitro alkanes in the presence of catalytic amounts of piperidine over 4 angstrom 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 synthesis of the Z isomer.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
