Abstract
Abstract(±)‐ω‐Halo‐α‐(chloroacetoxy)phosphonates were kinetically resolved by use of a protease (Chirazyme® P‐2). The esters recovered at levels of conversion between 56 and 72 % furnished (S)‐alcohols of 99 % ee. These were converted via azides into the phosphonic acid analogues of L‐lysine, L‐proline, L‐ornithine and L‐pipecolic acid. (–)‐Phosphaproline was transformed into crystalline ureas derived from (R)‐ and (S)‐1‐phenylethyl isocyanate. X‐ray structure analyses revealed that the levorotary phosphaproline has the R configuration, contrary to earlier reports.
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