A new reagent for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides. Synthesis of (R)- and (S) -β-carboxymethyl-β-methyl-β-lactones by asymmetric desymmetrization of HMGA anhydride

Article abstract of DOI:10.1016/0040-4039(96)00274-2

(R)- and (S)-βarboxymethyl-β-methyl-β-lactones, new reagents for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides were developed through the asymmetric desymmetrization of HMGA anhydride. The reagent was smoothly reactedwith various alkoxide without racemization to afford the desirable half-esters. On the other hand, the reaction with various amine in refluxing toluene gave a racemic amide. The chiral HMGA amide was prepared using the corresponding methyl ester of the reagent.