title: Calixpyrrole derivatives: "multi hydrogen bond" catalysts for gamma-butenolide synthesis.
abstract: Calix[4]pyrrole (1), calix[2]m-benzo[4]pyrrole (2), 10alpha,20beta- and 10alpha,20alpha- bis(4-nitrophenyl)-calix[4]pyrroles 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 gamma-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.
authors.affiliation: Department of Chemistry, University of Salerno, via Ponte don Melillo, 84084 Fisciano (SA), Italy.
authors.forename: Grazia
authors.initials: G
authors.lastname: Cafeo
authors.forename: Margherita
authors.initials: M
authors.lastname: De Rosa
authors.forename: Franz H
authors.initials: FH
authors.lastname: Kohnke
authors.forename: Annunziata
authors.initials: A
authors.lastname: Soriente
authors.forename: Carmen
authors.initials: C
authors.lastname: Talotta
authors.forename: Luca
authors.initials: L
authors.lastname: Valenti
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000447:Aldehydes / Q000737:chemistry; D047250:Calixarenes / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000737:chemistry; D006860:Hydrogen Bonding; D011166:Porphyrins / Q000737:chemistry*
chemical_list: C454640:2-trimethylsilyloxyfuran; D000447:Aldehydes; D005663:Furans; D011166:Porphyrins; C469811:calix(4)pyrrole; D047250:Calixarenes; C004511:butenolide; D015107:4-Butyrolactone