title: Design, Synthesis, and Conformational Analysis of Proposed β-Turn Mimics from Isoxazoline-Cyclopentane Aminols.
abstract: Constrained aminols from oxazanorbornene derivatives have the geometrical features to be used as β-turn inducers. Four different stereoisomers were prepared and spectroscopically characterized (MD calculations, NMR-titration and VT-NMR experiments). Temperature coefficients in DMSO are indicative for the existence of an intramolecular hydrogen bond. Chirooptical properties revealed a β-turn arrangement of all the synthesized compounds, where, depending on the absolute configuration of the cyclopentane spacer, they can be labeled as left- or right-handed turns.
authors.affiliation: Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 - Pavia (Italy).
authors.forename: Misal Giuseppe
authors.initials: MG
authors.lastname: Memeo
authors.affiliation: Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 - Pavia (Italy).
authors.forename: Mariella
authors.initials: M
authors.lastname: Mella
authors.affiliation: Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 - Pavia (Italy).
authors.forename: Valentina
authors.initials: V
authors.lastname: Montagna
authors.affiliation: Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 - Pavia (Italy). paolo.quadrelli@unipv.it.
authors.forename: Paolo
authors.initials: P
authors.lastname: Quadrelli
keywords: Diels-Alder reactions; amino alcohols; cycloadditions; nitrosocarbonyl compounds; β-turn inducers