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Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis
Department of Chemistry, University of Salerno, via Ponte don Melillo, 84084 Fisciano (SA), Italy
Department of Organic and Biological Chemistry, University of Messina, Salita Sperone 31, 98166 Messina, Italy
* Authors to whom correspondence should be addressed.
Received: 22 May 2009; in revised form: 7 July 2009 / Accepted: 9 July 2009 / Published: 15 July 2009
Abstract: Calixpyrrole (1), calixm-benzopyrrole (2), 10α,20β- and 10α,20α- bis(4-nitrophenyl)-calixpyrroles 3 and 4, respectively, were found to exhibit various organocatalytic activities in the diastereoselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF, 7) to aldehydes. The γ-hydroxybutenolide products are obtained in fairly good yields and with moderate diastereoselectivity. The structures of the catalysts, as well as the reaction conditions, strongly influence the efficiency of the reaction.
Keywords: calixpyrroles; diastereoselective synthesis; organocatalysis; aldol addition; 2-Trimethyl-silyloxyfuran
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Cafeo, G.; De Rosa, M.; Kohnke, F.H.; Soriente, A.; Talotta, C.; Valenti, L. Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis. Molecules 2009, 14, 2594-2601.
Cafeo G, De Rosa M, Kohnke FH, Soriente A, Talotta C, Valenti L. Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis. Molecules. 2009; 14(7):2594-2601.
Cafeo, Grazia; De Rosa, Margherita; Kohnke, Franz H.; Soriente, Annunziata; Talotta, Carmen; Valenti, Luca. 2009. "Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis." Molecules 14, no. 7: 2594-2601.