We report here a novel and simple method for the synthesis of α-amino-α′-hydroxyalkylphosphinic
acids in good yields in two simple steps without any protection–deprotection steps.
We have developed an efficient method for the synthesis of α-amino-α′-hydroxyalkylphosphinic
acids via the reaction of easily available α-hydroxyalkylphosphinic acids with diimines.
Treatment of α-hydroxyalkylphosphinic acids with diimines in the presence of trimethylsilyl
chloride (TMSCl) gives α-amino-α′-hydroxyalkylphosphinic acids in good yields. The
reaction gave a mixture of two diastereomeric forms of α-amino-α′-hydroxyalkylphosphinic
acids. The difference in solubility in organic solvents allowed us to readily separate
the diastereoisomers.
Key words
phosphinic acids - hydroxyalkylphosphinic acid - amino-α′-hydroxyalkylphosphinic acid
- diimines - bis(α-aminoalkyl)phosphinic acid