NEW ENANTIOMERICALLY PURE AMINOALCOHOLS FROM (R)-ALPHA-METHYLBENZYLAMINE AND CYCLOHEXENE OXIDE

Authors
BARBARO P BIANCHINI C SERNAU V
Citation
P. Barbaro et al., NEW ENANTIOMERICALLY PURE AMINOALCOHOLS FROM (R)-ALPHA-METHYLBENZYLAMINE AND CYCLOHEXENE OXIDE, Tetrahedron : asymmetry, 7(3), 1996, pp. 843-850
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
3
Year of publication
1996
Pages
843 - 850
Database
ISI
SICI code
0957-4166(1996)7:3<843:NEPAF(>2.0.ZU;2-H
Abstract
The new chiral aminoalcohols {(S)-[cyclohexan-(S)-2-ol]}-(R)-alpha-met hylbenzyl amine 1 and -{(R)-[cyclohexan-(R)-2-ol]}-(R)-alpha-methylami ne 2 were prepared by reaction of (R)-alpha-methylbenzylamine with cyc lohexene oxide at 160 degrees C. The diastereoisomers were separated b y fractional crystallization of the corresponding ammonium chlorides { (S)-[cyclohexan-(S)-2-ol]}-(R)-alpha-methylbenzyl ammonium chloride 1 . HCl and {(R)-[cyclohexan-(R)-2-ol]}-(R)-alpha-methylbenzyl ammonium chloride 2 . HCl. The absolute configuration of all stereocenters in 1 . HCl and 2 . HCl was determined by X-ray diffraction analyses. (C) 1 996 Elsevier Science Ltd