Design, Synthesis, and Conformational Analysis of Proposed β-Turn Mimics from Isoxazoline-Cyclopentane Aminols

• Published in: Chemistry : a European journal Vol. 21; no. 46; pp. 16374 - 16378
• Main Authors: Memeo, Misal Giuseppe, Mella, Mariella, Montagna, Valentina, Quadrelli, Paolo
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 09.11.2015; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Absolute configuration; amino alcohols; Chemistry; Conformational analysis; Constraints; cycloadditions; Cyclopentane; Derivatives; Diels-Alder reactions; Hydrogen bonds; Inducers; Mathematical analysis; nitrosocarbonyl compounds; NMR; Nuclear magnetic resonance; Spacers; Spectroscopy; Stereoisomerism; Stereoisomers; Titration; β-turn inducers; Diels-Alder reactions; cycloadditions; β-turn inducers; nitrosocarbonyl compounds; amino alcohols
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201503062

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. Constrained aminols from oxazanorbornene derivatives have the geometrical features to be used as β‐turn inducers (see figure). Four different stereoisomers were prepared and spectroscopically characterized (MD calculations, NMR‐titration, and VT‐NMR experiments).