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

<A NAME="RZ15707SS-1A">1a</A> Rosini G. Ballini R. Synthesis 1988, 833

<A NAME="RZ15707SS-1B">1b</A> Ono N. The Nitro Group in Organic Synthesis Wiley-VCH; New York: 2001.

<A NAME="RZ15707SS-1C">1c</A> Ballini R. Bosica G. Fiorini D. Palmieri A. Petrini M. Chem. Rev. 2005, 105: 933

<A NAME="RZ15707SS-2A">2a</A> Seebach D. Colvin EW. Lehr F. Weller T. Chimia 1979, 33: 1

<A NAME="RZ15707SS-2B">2b</A> Ballini R. Petrini M. Tetrahedron 2004, 60: 1017

<A NAME="RZ15707SS-3A">3a</A> Barnes DM. Ji JG. Fickes MG. Fitzgerald MA. King SA. Morton HE. Plagge FA. Preskill M. Wagaw SH. Wittenberger SJ. Zhang J. J. Am. Chem. Soc. 2002, 124: 13097

<A NAME="RZ15707SS-3B">3b</A> Hoashi Y. Yabuta T. Takemoto Y. Tetrahedron Lett. 2004, 45: 9185

<A NAME="RZ15707SS-4A">4a</A> Yanami T. Ballatore A. Miyashita M. Kato M. Yoshikoshi A. Synthesis 1980, 407

<A NAME="RZ15707SS-4B">4b</A> Gómez-Sánchez A. Stiefel BM. Fernández-Fernández R. J. Chem. Soc., Perkin Trans. 1 1982, 441

<A NAME="RZ15707SS-4C">4c</A> Watanabe M. Ikagawa A. Wang H. Murata K. Ikariya T. J. Am. Chem. Soc. 2004, 126: 11148

<A NAME="RZ15707SS-4D">4d</A> Li H. Wang L. Tang L. Deng L. J. Am. Chem. Soc. 2004, 126: 9906

<A NAME="RZ15707SS-4E">4e</A> Ji J. Barnes DM. Zhang J. King SA. Wittenberger SJ. Morton HE. J. Am. Chem. Soc. 1999, 121: 10215

<A NAME="RZ15707SS-4F">4f</A> Wang J. Li H. Duan W. Zu L. Wang W. Org. Lett. 2005, 7: 4713

<A NAME="RZ15707SS-4G">4g</A> Terada M. Ube H. Yaguchi Y. J. Am. Chem. Soc. 2006, 128: 1454

<A NAME="RZ15707SS-4H">4h</A> Evans D. Seidel D. J. Am. Chem. Soc. 2005, 127: 9958

<A NAME="RZ15707SS-4I">4i</A> Okino T. Hoashi Y. Furukawa T. Xu X. Takemoto Y. J. Am. Chem. Soc. 2005, 127: 119

<A NAME="RZ15707SS-5">5</A> Shirakava S. Kobayashi S. Synlett 2006, 1410

<A NAME="RZ15707SS-6">6</A> Fei CP. Chan TH. Chan TH. Synthesis 1982, 467

<A NAME="RZ15707SS-7A">7a</A> Paszlo P. Acc. Chem. Res. 1986, 19: 121

<A NAME="RZ15707SS-7B">7b</A> Ley SV. Baxendale IR. Bream RN. Jackson PS. Leach AG. Longbottom DA. Nesi M. Scott JS. Storter RJ. Taylor SJ. J. Chem. Soc., Perkin Trans. 1 2000, 3815

<A NAME="RZ15707SS-7C">7c</A> Chakrabarty M. Bsak R. Ghosh N. Tetrahedron Lett. 2001, 42: 3913

<A NAME="RZ15707SS-7D">7d</A> de la Hoz A. Daz-Ortiz A. Gomez MV. Mayoral JA. Moreno A. Sanchez-Millagon AM. Vasquez E. Tetrahedron 2001, 57: 5421

<A NAME="RZ15707SS-7E">7e</A> Michaud D. Texier-Boullet F. Hamelin J. Tetrahedron Lett. 1997, 38: 7563

<A NAME="RZ15707SS-8A">8a</A> Sartori G. Ballini R. Bigi F. Bosica G. Maggi R. Righi P. Chem. Rev. 2004, 104: 199

<A NAME="RZ15707SS-8B">8b</A> Ballini R. Palmieri A. Curr. Org. Chem. 2006, 10: 2145

<A NAME="RZ15707SS-9A">9a</A> Ballini R. Barboni L. Fiorini D. Giarlo G. Green Chem. 2005, 7: 828

<A NAME="RZ15707SS-9B">9b</A> Ballini R. Rabanedo Clemente R. Palmieri A. Petrini M. Adv. Synth. Catal. 2006, 348: 191

<A NAME="RZ15707SS-9C">9c</A> Ballini R. Palmieri A. Adv. Synth. Catal. 2006, 348: 1154

<A NAME="RZ15707SS-9D">9d</A> Ballini R. Fiorini D. Maggi R. Oro C. Palmieri A. Sartori G. Synlett 2006, 1849