Configurational and conformational NMR study of enantiopure 2,2-dimethyl-1-(1-naphthyl)propanol via its carbamate derivatives

Authors
Pomares, M Grabuleda, X Jaime, C Virgili, A Alvarez-Larena, A Piniella, JF
Citation
M. Pomares et al., Configurational and conformational NMR study of enantiopure 2,2-dimethyl-1-(1-naphthyl)propanol via its carbamate derivatives, MAGN RES CH, 37(12), 1999, pp. 885-890
Citations number
21
Categorie Soggetti
Spectroscopy /Instrumentation/Analytical Sciences
Journal title
MAGNETIC RESONANCE IN CHEMISTRY
ISSN journal
07491581 → ACNP
Volume
37
Issue
12
Year of publication
1999
Pages
885 - 890
Database
ISI
SICI code
0749-1581(199912)37:12<885:CACNSO>2.0.ZU;2-1
Abstract
2,2-Dimethyl-1-(1-naphthyl)propanol was synthesized and the corresponding e nantiomers were isolated by chiral HPLC. These enantiomers gave diastereois omeric carbamates by reaction with (S)-(-)-1-phenylethylisocyanate, which w ere studied by NMR. The comparison of NMR data and molecular mechanics calc ulations allowed us to determine the absolute configuration of correspondin g alcohols. Finally, x-ray results were in agreement with the absolute conf iguration proposed from the NMR spectra. Copyright (C) 1999 John Wiley & So ns, Ltd.