Preparation of optically active 2-aminoalkylphosphinic and phosphonic acids

✍ Scribed by Mark E. Duggan; Donald S. Karanewsky

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 192 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)88062-4

✦ Synopsis

The reaction of sodium alkylphosphinates or sodium dialkylphosphonates with tosylamino tosylates of amino alcohols derived from 1-aminoalkylcarboxylic acids gives high yields of optically active Z-tosylaminoalkylphosphinic or phosphonic esters. Since the discovery of S-ethylaminophosphonic acid in various organisms, 1 the aminophosphonic acids have attracted considerable interest as replacements for the natural amino acids in various peptides 2a-d and in peptide-based enzyme inhibitors. 2e-g Although several general methods for the preparation of 1-aminoalkylphosphonic acids have been reported,3 relatively few reports have involved the synthesis of 2-aminoalkylphosphonic acids. 4 To our knowledge, 2-aminoalkylphosphonic acids have never been prepared in optically active form.

We wish to report an efficient synthesis of optically active 2-aminoalkylphosphinic & and phosphonic 2 acids from 2-aminoalcohols $ prepared by reduction 5 of the readily available optically active amino acids 2.