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Configurational and conformational NMR study of enantiopure 2,2‐dimethyl‐1‐(1‐naphthyl)propanol via its carbamate derivatives
Author(s) -
Pomares Marta,
Grabuleda Xavier,
Jaime Carlos,
Virgili Albert,
ÁlvarezLarena Ángel,
Piniella Joan F.
Publication year - 1999
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199912)37:12<885::aid-mrc572>3.0.co;2-6
Subject(s) - chemistry , enantiopure drug , enantiomer , absolute configuration , carbon 13 nmr , proton nmr , nuclear magnetic resonance spectroscopy , computational chemistry , chiral column chromatography , chiral derivatizing agent , organic chemistry , stereochemistry , enantioselective synthesis , catalysis
2,2‐Dimethyl‐1‐(1‐naphthyl)propanol was synthesized and the corresponding enantiomers were isolated by chiral HPLC. These enantiomers gave diastereoisomeric carbamates by reaction with ( S )‐(−)‐1‐phenylethyliso‐cyanate, which were studied by NMR. The comparison of NMR data and molecular mechanics calculations allowed us to determine the absolute configuration of corresponding alcohols. Finally, x‐ray results were in agreement with the absolute configuration proposed from the NMR spectra. Copyright © 1999 John Wiley & Sons, Ltd.