A New General Method To Obtain Chiral 2-Alkylglycidyl Acid Derivatives: Synthesis of Methyl (R)-(+)-Palmoxirate

Article abstract of DOI:10.1021/jo00082a008

The hydrolysis of the diastereomerically pure cyanohydrins, obtained by reaction of Et2AlCN with homochiral α-sulfinyl ketones, yielded β-sulfenyl esters or amides, which evolved into the corresponding 2-alkylglycidic acid derivatives (ee >97percent) by treatment with Me3O(1+)BF4(1-) and NaHCO3.The use of this sequence to synthesize optically pure (R)-(+)-palmoxirate, a powerful hypoglicemic agent, is also described.