Synthesis of Homochiral 4-Amino-4-carboxy-2-phosphonomethylpyrrolidines via a Diastereoselective Bucherer-Bergs Reaction of 4-Oxopyrrolidine Derivative: Novel Conformationally Restricted AP 5 Analogues

Article abstract of DOI:10.1016/0957-4166(95)00302-6

Asymmetric synthesis of 4-amino-4-carboxy-2-phosphonomethylpyrrolidines 1 and 2, which can be viewed as novel conformationally restricted analogues of 2-amino-5-phosphonopentanoic acid (AP 5) incorporated into the pyrrolidine ring, was achieved from trans-4-hydroxy-L-proline as a homochiral starting material using the diastereoselective Bucherer-Bergs reaction of (2S)-1-benzyl-2-<(diisopropylphosphonyl)methyl>-4-oxopyrrolidine 12.