Preparation of enantiomers of 1-(1-naphthyl)-2,2-dimethylpropylamine and their behaviour as chiral solvating agents: study of diastereochemic association by Job's plots and intermolecular NOE measurements

Enantiomers of 1-(1-naphthyl)-2,2-dimethylpropylamine have been obtained and considered as chiral solvating agents against several compounds. The formed complexes have been studied with the aid of the nuclear Overhauser effect and its stoichiometry by the method of continuous variations. Two diaster...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2000-09, Vol.11 (18), p.3747-3757
Main Authors: Port, A, Virgili, A, Alvarez-Larena, A, Piniella, J.F
Format: Article
Language:English
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Summary:Enantiomers of 1-(1-naphthyl)-2,2-dimethylpropylamine have been obtained and considered as chiral solvating agents against several compounds. The formed complexes have been studied with the aid of the nuclear Overhauser effect and its stoichiometry by the method of continuous variations. Two diastereoisomeric complexes present similar geometry of association by π–π-stacking of the aromatic rings and by hydrogen bonding of the functional groups.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(00)00334-7