ASYMMETRIC-SYNTHESIS OF ALPHA-HYDROXY-PHOSPHONAMIDES, PHOSPHONATES AND PHOSPHONIC-ACIDS

Authors
BLAZIS VJ KOELLER KJ SPILLING CD
Citation
Vj. Blazis et al., ASYMMETRIC-SYNTHESIS OF ALPHA-HYDROXY-PHOSPHONAMIDES, PHOSPHONATES AND PHOSPHONIC-ACIDS, Tetrahedron : asymmetry, 5(4), 1994, pp. 499-502
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
4
Year of publication
1994
Pages
499 - 502
Database
ISI
SICI code
0957-4166(1994)5:4<499:AOAPA>2.0.ZU;2-2
Abstract
The addition of the anion of the bicyclic chiral phosphorous acid diam ide 1a to aldehydes in THF solution gave alpha-hydroxy phosphonamides in good yield and good diastereoselectivity (54-93% de). The phosphona mides were hydrolyzed with aqueous HCl in dioxane to give alpha-hydrox y phosphonic acids. Methylation of the resulting phosphonic acids with diazomethane gave alpha-hydroxy dimethyl phosphonates without loss of stereochemical integrety.