Lipase-catalyzed enantioselective acylation of prochiral 2-(ω)-phosphono)alkyl-1,3-propanediols: Application to the enantioselective synthesis of ω-phosphono-α-amino acids

Article abstract of DOI:10.1016/0957-4166(96)00354-0

Lipase PS catalyzed acetylation of prochiral 2-(ω-phosphono)alkyl-1,3-propanediols 1a-c was found to proceed with high enantioselectivity. The applications of phosphonic chirons 2a-c thus obtained were illustrated by the stereocontrolled synthesis of ω-phosphono-α-amino acids such as L-AP-3, L-AP-4, and N-Boc-L-F₂Pab(OEt)₂-OH.