Lipase-Catalyzed Kinetic Resolution of Dimethyl and Dibutyl 1-Butyryloxy-1-carboxymethylphosphonates

The main objective of this study is the enantioselective synthesis carboxyhydroxyphosphonates by lipase-catalyzed reactions. For purpose, racemic dimethyl and dibutyl 1-butyryloxy-1-carboxymethylphosphonates were synthesized hydrolyzed, using a wide spectrum commercially available lipases from different sources (e.g., fungi bacteria). best hydrolysis results 1-butyryloxy-1-carboxymethylphosphonate obtained with use Candida rugosa, antarctica, Aspergillus niger, leading to optically active 1-carboxy-1-hydroxymethylphosphonate (58%–98% enantiomeric excess) high ratio (reaching up 126). However, in case 1-butyryloxy-1-carboxymethylphosphonate, Burkholderia cepacia Termomyces lanuginosus, (66%–68% moderate 8.6). absolute configuration products after biotransformation was also determined. In most cases, hydrolyzed (R) enantiomers both compounds.