Acidic Alumina as a Useful Heterogeneous Catalyst in the Michael Reaction of β-Dicarbonyl Derivatives with Conjugated Nitroalkenes

Roberto Ballini; Raimondo Maggi; Alessandro Palmieri; Giovanni Sartori

doi:10.1055/s-2007-983897

PAPER

Acidic Alumina as a Useful Heterogeneous Catalyst in the Michael Reaction of β-Dicarbonyl Derivatives with Conjugated Nitroalkenes

Roberto Ballini*^a, Raimondo Maggi^b, Alessandro Palmieri^a, Giovanni Sartori^b
^a Green Chemistry Group, Dipartimento di Scienze Chimiche, Università, Via S. Agostino 1, 62032 Camerino (MC), Italy
Fax: +39(0737)402297; e-Mail: roberto.ballini@unicam.it;
^b Clean Synthetic Methodologies Group, Dipartimento di Chimica Organica e Industriale, Università, Consorzio Interuniversitario ‘La Chimica per l"Ambiente’ (INCA), UdR di Parma 2, Viale G.P. Usberti 17A, 43100 Parma, Italy

Abstract

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Abstract

Addition of a variety of 1,3-dicarbonyl derivatives to conjugated nitroalkenes was efficiently performed under heterogeneous catalysis by acidic alumina in the presence of a minimum amount of solvent (Et₂O, 0.5 mL/mmol). The procedure allows satisfactory to good yields of a diastereomeric mixture (˜1:1) of polyfunctionalized adducts. Moreover, work-up can be avoided since the reaction mixture can be directly charged into a chromatographic column for immediate purification.

Key words

acidic alumina - conjugated nitroalkenes - Michael reaction - heterogeneous catalysis - eco-friendly synthesis

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References

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