1294449-05-0Relevant articles and documents
Chemoenzymatic synthesis of phosphonic acid analogues of L-lysine, L-proline, L-ornithine, and L-pipecolic acid of 99 % ee - Assignment of absolute configuration to (-)-proline
Wuggenig, Frank,Schweifer, Anna,Mereiter, Kurt,Hammerschmidt, Friedrich
, p. 1870 - 1879 (2011/05/05)
(±)-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. Copyright