CONTROLLED REGIOSELECTIVE ANILIDE FORMATION FROM ASPARTIC AND GLUTAMIC-ACID ANHYDRIDES

The regioselectivity of the reaction of aniline with a series of N-pro tected aspartic and glutamic acid anhydrides was controlled through th e choice of reaction solvent. In benzene, the formation of aspartic or glutamic acid a-anilides was favored, with alpha:(beta or gamma) regi oselectivities as high as 100:0. On the other hand, in DMSO, the forma tion of either aspartic acid beta-anilide or glutamic acid gamma-anili de was favored, with alpha:(beta or gamma) regioselectivities as high as 0:100. This regioselectivity was not observed for alkylamines, amin o acids, thiols, or alcohols. However, the high yields of the aniline reactions and the ability to specify their regioselectivities demonstr ate the usefulness of our method for the formation of aspartic and glu tamic acid anilide bonds.