Abstract
Racemic α-chloracetoxyphosphonates 1 were kinetically resolved using protease Chirazyme® P-2 or lipase SP 524 in a well stirred biphasic system keeping the pH constant at 7.0 by automatic addition of 0.5 M NaOH. Lipase SP 524 hydrolyses preferentially the(S)-ester la (R = C2H5), protease Chirazyme® P-2 the (R)-esters 1. The chiral, non-racemic esters (S)-1, isolated after stopping the reactions at appropriate conversions, were hydrolysed with MeOH/NEt3 and then transformed to the corresponding 1-azidophosphonates using Ph3P/DEAD/HN3. The azides were reduced with H2/Pd/C deprotected with refluxing 6M HCl to give phosphonic acids (R)-3[1,2].
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