Asymmetric synthesis of N-protected chiral 1-aminoalkylphosphonic acids and synthesis of side chain-functionalized depsiphosphonopeptides

Abstract

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 directly from one-pot reactions of benzyl carbamate, aldehydes, and diethyl (R,R)-2-chloro-1,3,2-dioxaphospholane-4,5-dicarboxylate. Copyright © 2005 European Peptide Society and John Wiley & Sons, Ltd.