Asymmetric Synthesis of α-Amino Phosphonic Acids by Diastereoselective Addition of Trimethyl Phosphite onto Chiral Oxazolidines1
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (11) , 3687-3693
- https://doi.org/10.1021/jo960020c
Abstract
A simple and general asymmetric synthesis of α-amino phosphonic acids is described. The method involves the highly selective addition of trialkyl phosphite onto various chiral oxazolidines. Oxazaphosphorinanes thus obtained with an excellent diastereoselectivity furnish the corresponding (S)-α-substituted amino phosphonic acids in good overall yields and high ee (77→97%) after simple deprotection.Keywords
This publication has 10 references indexed in Scilit:
- A simple and general method for the asymmetric synthesis of α-aminophosphonic acidsTetrahedron Letters, 1992
- An improved, convenient procedure for reduction of amino acids to aminoalcohols: Use of NaBH4-H2SO4Tetrahedron Letters, 1992
- Catalysis of aryl-halogen exchange by nickel(II) complexes using sodium hypochloriteThe Journal of Organic Chemistry, 1991
- Ring-chain tautomerism of 1,3-oxazolidines prepared from norephedrine and norpseudoephedrineTetrahedron, 1989
- OPTICALLY ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDSPhosphorus, Sulfur, and Silicon and the Related Elements, 1987
- Stereochemistry-60Tetrahedron, 1985
- Hydroxy schiff base-oxazolidine tautomerism: Apparent breakdown of baldwin's rulesTetrahedron, 1985
- Aqueous solution conformation of rigid nucleosides and nucleotidesJournal of the American Chemical Society, 1976
- Conformational analysis of 2-phospha-1,3-dithiacyclohexanes. Further evidence for the general axial preference of phosphorus substituents in saturated six-membered ringsJournal of the American Chemical Society, 1972
- Some Comments on a Reported Quinuclidine Synthesis.Acta Chemica Scandinavica, 1967