Preparation of 1-aminoalkylphosphonic acids and 2-aminoalkylphosphonic acids by reductive amination of oxoalkylphosphonates
✍ Scribed by Artur Ryglowski; Pawel Kafarski
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 389 KB
- Volume
- 52
- Category
- Article
- ISSN
- 0040-4020
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## Abstract __N__,__N__′‐Alkylidenebisamides 1, totally unsuitable as amidoalkylating agents toward phosphorous acid, react with its “activated” form prepared “in situ” from phosphorus(III) chloride and acetic acid to give the desired 1‐aminoalkylphosphonic acids 2 in high yields.
Optically active 1-aminoalkylphosphonic acid derivatives were synthesized in moderate yields and optical purities via Mannich-type reactions of benzyl carbamate, aldehydes, and optically pure chlorophosphites. Side chain-functionalized depsiphosphonopeptides were also prepared in satisfactory yields
A convenient 31P NMR method for determining the enantiomeric excess of free 1-aminoalkylphosphonic acids is presented. It was found by NMR that the interaction of Pd" ions with 1-aminophosphonate ligands (L) yields, in a non-diastereoselective manner, diastereoisomeric chelate pairs (PdL,) observabl