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Design, Synthesis, and Conformational Analysis of Proposed β‐Turn Mimics from Isoxazoline‐Cyclopentane Aminols
Author(s) -
Memeo Misal Giuseppe,
Mella Mariella,
Montagna Valentina,
Quadrelli Paolo
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503062
Subject(s) - cyclopentane , intramolecular force , turn (biochemistry) , chemistry , titration , hydrogen bond , proton nmr , stereochemistry , molecule , organic chemistry , biochemistry
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.