Asymmetric synthesis of α-substituted alkylphosphonates based on symmetrical dialkyl phosphites

Article abstract of DOI:10.1007/BF02496414

Chiral C₂-symmetrical dialkyl phosphites and C₃-symmetrical trialkyl phosphites, derived from (-)-borneol, (-)-menthol, and 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, were studied as the starting reagents for the preparation of chiral organophosphorus compounds. The reactions of C₂-symmetrical dialkyl phosphites and C₃-symmetrical trialkyl phosphites with aldehydes and amines or aldehydes are accompanied by asymmetrical induction at the α-carbon atom to yield optically active α-aminoalkylphosphonates or α-hydroxyalkylphosphonates, respectively. The stereoselectivity of the reaction depends on the structure of the starting compounds and the reaction conditions.