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.
2008
conjugated nitro alkenes; henry reaction; nitro compounds
01 Pubblicazione su rivista::01a Articolo in rivista
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]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/226281
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