ACCÈS [Agrave] L'ACIDE AMINO-2 PROPYLPHOSPHONIQUE OPTIQUEMENT ACTIF

Abstract

The reaction of optically active α-methylbenzylamine with phosphonates containing an unsaturated carbon in the β position results in a mixture of cis- and trans-aminovinylphosphonates. Reduction with NaBH₄/CH₃COOH/THF produces benzylaminopropylphosphonates in good yield and stereoselectivity (72%); the selectivity is closely dependent on the phosphorus environment. Reduction with hydrogen in the presence of Pd/C as catalyst gives better selectivity (90%); however, the reaction is limited to phosphonates bearing a t-Bu substituent. After hydrolysis, debenzylation and purification, we isolated optically active 2-aminopropylphosphonic acid. The rotations are reported.