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

A. Port, A. Virgili, A. Alvarez Alvarez-Larena, J. F. Piniella

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Abstract

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. © 2000 Elsevier Science Ltd.
Original languageEnglish
Pages (from-to)3747-3757
JournalTetrahedron Asymmetry
Volume11
Issue number18
DOIs
Publication statusPublished - 22 Sep 2000

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