title: A Simple Tetraminocalix[4]arene as a Highly Efficient Catalyst under "On-Water" Conditions through Hydrophobic Amplification of Weak Hydrogen Bonds.
abstract: The simple tetraminocalix[4]arene 1, which contains weak H-bond-donor NH2groups, is reported to be a highly efficient organocatalyst for the Vinylogous Mukaiyama Aldol Reaction (VMAR) of 2-(trimethylsilyloxy)furan 5 with α-ketoesters 6 a-l under "on-water" conditions owing to the hydrophobic amplification of weak H-bond interactions. The catalytic efficiency of calixarene catalyst 1 was shown to be closely related to its recognition abilities towards the reactants 5 and 6 through a multipoint recognition model. The proposed model provided good explanations for the differences on the reaction rate acceleration and on the stereoselectivity observed with different substrates.
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università degli Studi di Salerno, Via Ponte don Melillo, 84084, Fisciano (SA), Italy.
authors.forename: Margherita
authors.identifier: http://orcid.org/0000-0001-7451-5523
authors.initials: M
authors.lastname: De Rosa
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università degli Studi di Salerno, Via Ponte don Melillo, 84084, Fisciano (SA), Italy.
authors.forename: Pellegrino
authors.initials: P
authors.lastname: La Manna
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università degli Studi di Salerno, Via Ponte don Melillo, 84084, Fisciano (SA), Italy.
authors.forename: Annunziata
authors.initials: A
authors.lastname: Soriente
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università degli Studi di Salerno, Via Ponte don Melillo, 84084, Fisciano (SA), Italy.
authors.forename: Carmine
authors.initials: C
authors.lastname: Gaeta
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università degli Studi di Salerno, Via Ponte don Melillo, 84084, Fisciano (SA), Italy.
authors.forename: Carmen
authors.initials: C
authors.lastname: Talotta
authors.affiliation: Centro di Eccellenza in Biocristallografia, Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Trieste, via L. Giorgieri 1, 34127, Trieste, Italy.
authors.forename: Neal
authors.initials: N
authors.lastname: Hickey
authors.affiliation: Centro di Eccellenza in Biocristallografia, Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Trieste, via L. Giorgieri 1, 34127, Trieste, Italy.
authors.forename: Silvano
authors.initials: S
authors.lastname: Geremia
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università degli Studi di Salerno, Via Ponte don Melillo, 84084, Fisciano (SA), Italy.
authors.forename: Placido
authors.initials: P
authors.lastname: Neri
keywords: aldol reaction; calixarenes; hydrophobic effect; organocatalysts; supramolecular chemistry