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

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

doi:10.1002/(SICI)1097-458X(199912)37:12<885::AID-MRC572>3.0.CO;2-6

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

Marta Pomares, Xavier Grabuleda, Carlos Jaime, Albert Virgili, Ángel Álvarez-Larena, Joan F. Piniella

Research output: Contribution to journal › Article › Research › peer-review

3 Citations (Scopus)

Abstract

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. Copyright © 1999 John Wiley & Sons, Ltd.

Original language	English
Pages (from-to)	885-890
Journal	Magnetic Resonance in Chemistry
Volume	37
Issue number	12
DOIs	https://doi.org/10.1002/(SICI)1097-458X(199912)37:12<885::AID-MRC572>3.0.CO;2-6
Publication status	Published - 1 Jan 1999

Keywords

1 H NMR
Carbamates
Chiral HPLC
Molecular mechanics (MM)
NMR
X-ray

Access to Document

10.1002/(SICI)1097-458X(199912)37:12<885::AID-MRC572>3.0.CO;2-6

Cite this

@article{ee72e4b546d1433d898afabfbfb2c0b4,

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

abstract = "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. Copyright {\textcopyright} 1999 John Wiley & Sons, Ltd.",

keywords = "1 H NMR, Carbamates, Chiral HPLC, Molecular mechanics (MM), NMR, X-ray",

author = "Marta Pomares and Xavier Grabuleda and Carlos Jaime and Albert Virgili and {\'A}ngel {\'A}lvarez-Larena and Piniella, {Joan F.}",

year = "1999",

month = jan,

day = "1",

doi = "10.1002/(SICI)1097-458X(199912)37:12<885::AID-MRC572>3.0.CO;2-6",

language = "English",

volume = "37",

pages = "885--890",

number = "12",

}

TY - JOUR

T1 - Configurational and conformational NMR study of enantiopure 2,2-dimethyl-1-(1-naphthyl)propanol via its carbamate derivatives

AU - Pomares, Marta

AU - Grabuleda, Xavier

AU - Jaime, Carlos

AU - Virgili, Albert

AU - Álvarez-Larena, Ángel

AU - Piniella, Joan F.

PY - 1999/1/1

Y1 - 1999/1/1

N2 - 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. Copyright © 1999 John Wiley & Sons, Ltd.

AB - 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. Copyright © 1999 John Wiley & Sons, Ltd.

KW - 1 H NMR

KW - Carbamates

KW - Chiral HPLC

KW - Molecular mechanics (MM)

KW - NMR

KW - X-ray

U2 - 10.1002/(SICI)1097-458X(199912)37:12<885::AID-MRC572>3.0.CO;2-6

DO - 10.1002/(SICI)1097-458X(199912)37:12<885::AID-MRC572>3.0.CO;2-6

M3 - Article

VL - 37

SP - 885

EP - 890

IS - 12

ER -

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

Abstract

Keywords

Access to Document

Fingerprint

Cite this