Preparation of Optically Active 1-Aminoalkylphosphonic Acids from Chiral Carbamates and Chiral Ureas

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Abstract
Optically active 1-aminoalkylphosphonic acids were successfully synthesized from chiral carbamate and urea derivatives which were prepared from such chiral substrates as (−)-menthol, (+)-camphor, and (R)-(+)-and (S)-(−)-(1-phenylethyl)ureas by the actions of aldehydes and triaryl phosphites. 1-Aminoalkylphosphonic acid derivatives, thus prepared, have an (R)-(+)- or (S)-(−)-configuration, depending on the chiral source via a retention of the configuration; i.e., (+)-products were prepared from chiral (+)-carbamate and (+)-urea derivatives, and (−)-products from chiral (−)-carbamate and (−)-urea derivatives.