Ready N-alkylation of enantiopure aminophenols: synthesis of tertiary aminophenols

Authors
Cimarelli, C Palmieri, G Volpini, E
Citation
C. Cimarelli et al., Ready N-alkylation of enantiopure aminophenols: synthesis of tertiary aminophenols, TETRAHEDRON, 57(28), 2001, pp. 6089-6096
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
28
Year of publication
2001
Pages
6089 - 6096
Database
ISI
SICI code
0040-4020(20010709)57:28<6089:RNOEAS>2.0.ZU;2-3
Abstract
A regioselective indirect alkylation of aminophenols to enantiopure tertiar y aminophenols, which are useful chiral ligands for metal-catalysed asymmet ric reactions, is reported. This very simple synthetic methodology, through reduction or alkylation of an intermediate benzoxazine, was performed in m ild conditions, suitable for the conservation of the configuration of the s tereogenic centres. Some crystalline aminophenols show the phenomenon of 'c rystallization-induced asymmetric transformation'. (C) 2001 Elsevier Scienc e Ltd. All rights reserved.