Nitroalkanes as Central Reagents in the Synthesis of Spiroketals

doi:10.3390/molecules13020319

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Molecules 2008, 13(2), 319-330; doi:10.3390/molecules13020319

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Nitroalkanes as Central Reagents in the Synthesis of Spiroketals

Roberto Ballini ¹^,* , Marino Petrini ¹ and Goffredo Rosini ²

¹ Dipartimento di Scienze Chimiche, Università di Camerino, via S.Agostino, 1, I-62032 Camerino, Italy ² Dipartimento di Chimica Organica ‘A. Mangini’, Alma Mater Studiorum–Università di Bologna, Viale del Risorgimento n. 4, 40136 Bologna, Italy

* Author to whom correspondence should be addressed.

Received: 8 January 2008; in revised form: 2 February 2008 / Accepted: 4 February 2008 / Published: 7 February 2008

(This article belongs to the Special Issue Spiro Compounds)

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Abstract: Nitroalkanes can be profitably employed as carbanionic precursors for theassembly of dihydroxy ketone frameworks, suitable for the preparation of spiroketals. Thecarbon-carbon bond formation is carried out exploiting nitroaldol and Michael reactions,while the nitro to carbonyl conversion (Nef reaction) ensures the correct introduction of theketo group. Several spiroketal systems endowed with considerable biological activity canbe prepared using this synthetic strategy.

Keywords: Conjugate addition; Nef reaction; nitroaldol reaction; nitroalkanes; spiroketals.

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MDPI and ACS Style

Ballini, R.; Petrini, M.; Rosini, G. Nitroalkanes as Central Reagents in the Synthesis of Spiroketals. Molecules 2008, 13, 319-330.

AMA Style

Ballini R., Petrini M., Rosini G. Nitroalkanes as Central Reagents in the Synthesis of Spiroketals. Molecules. 2008; 13(2):319-330.

Chicago/Turabian Style

Ballini, Roberto; Petrini, Marino; Rosini, Goffredo. 2008. "Nitroalkanes as Central Reagents in the Synthesis of Spiroketals." Molecules 13, no. 2: 319-330.

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