ALPHA-AMINOPHOSPHONATES BEARING FREE HYDROXYL-GROUPS IN THE AROMATIC RINGS - SYNTHESIS AND NMR CHARACTERIZATION

Authors
FAILLA S FINOCCHIARO P HAGELE G KALCHENKO VI
Citation
S. Failla et al., ALPHA-AMINOPHOSPHONATES BEARING FREE HYDROXYL-GROUPS IN THE AROMATIC RINGS - SYNTHESIS AND NMR CHARACTERIZATION, Phosphorus, sulfur and silicon and the related elements, 128, 1997, pp. 63-77
Citations number
30
Journal title
Phosphorus, sulfur and silicon and the related elements → ACNP
ISSN journal
10426507
Volume
128
Year of publication
1997
Pages
63 - 77
Database
ISI
SICI code
1042-6507(1997)128:<63:ABFHIT>2.0.ZU;2-1
Abstract
In this paper we describe a useful synthetic procedure leading in very good yields to mono- and bis-alpha-aminophosphonic acid dialkylesters containing the free phenolic hydroxyl group in a strategic position o f the aromatic ring in order to enhance complexation with metal ions. This synthetic procedure is based on the addition of a solution of sod ium dialkyl phosphite in phosphite to imine precursors. The addition r eaction is highly stereospecific: only one diastereomer for each of th e bis-alpha-aminophosphonic acid dialkylesters is formed. All compound s were characterized by NMR (H-1 and P-31) and by FAB-MS spectroscopy.