Asymmetric Synthesis of D-(E)-2-Amino-5-phosphono-3-pentenoic Acid (APPA) by Using a Chiral Auxiliary

Abstract

The synthesis of D-2-amino-5-phosphono-3-pentenoic acid (1) is reported. The key intermediate, a (2R, 3S)-3-hydroxyallylglycine derivative (8), was prepared by the reaction of (5S)-3, 6-dimethoxy-5-isopropyl-2, 4-dihydropyrazine (2) and acrolein in the presence of chlorotitanium tris(diethylamide). The transformation of 8 into 1 via allylic alcohol 11 was carried out by following the reported route.