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

✍ Scribed by Marta Pomares; Xavier Grabuleda; Carlos Jaime; Albert Virgili; Ángel Álvarez-Larena; Joan F. Piniella

• Book ID: 101252790
• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 101 KB
• Volume: 37
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/(sici)1097-458x(199912)37:12<885::aid-mrc572>3.0.co;2-6

✦ Synopsis

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-phenylethylisocyanate, 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.