Abstract
AbstractWe report here the first diastereoselective synthesis of (2S,5R)‐5‐methyl‐5‐(phosphono)‐proline, a phosphoproline derivative from L‐pyroglutamic acid. The main feature of this methodology is the transformation of L‐pyroglutamic acid into chiral cyclic imines as a versatile intermediate followed by diastereoselective nucleophilic addition of trialkyl phosphites or diethyl phosphite in the presence of PhB(OH)2, Ph2P(O)OH, (PhO)2P(O)OH, Ph(H)P(O)OH and TiCl4. N‐Cbz Cleavage with simultaneous hydrolysis of phosphonate and carboxylate esters in the quaternary cyclic α‐aminophosphonate, gave the target compound.
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