A NEW REAGENT FOR THE PREPARATION OF CHIRAL HMGA (3-HYDROXY-3-METHYLGLUTARIC ACID) ESTERS AND AMIDES - SYNTHESIS OF (R)-BETA-CARBOXYMETHYL-BETA-METHYL-BETA-LACTONE AND (S)-BETA-CARBOXYMETHYL-BETA-METHYL-BETA-LACTONE BY ASYMMETRIC DESYMMETRIZATION OF HMGA ANHYDRIDE

(R)- and (S)-beta-carboxymethyl-beta-methyl-beta-lactones, new reagent s for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides were developed through the asymmetric desymmetrizat ion of HMGA anhydride. The reagent was smoothly reacted with various a lkoxide without racemization to afford the desirable half-esters. On t he other hand, the reaction with various amine in refluxing toluene ga ve a racemic amide, The chiral HMGA amide was prepared using the corre sponding methyl ester of the reagent.