Optically pure beta-substituted beta-hydroxy aspartates as glutamate transporter blockers.

A short asymmetric synthesis of optically pure beta-substituted beta-hydroxy aspartates is described. The key step is an aldol reaction between a glycine enolate derived from an oxazinone intermediate used as chiral auxiliary and various alpha-keto esters. Excellent diastereomeric excesses are obtained.

An intermediate in a new synthesis approach to beta-substituted beta-hydroxyaspartame.

The crystal and molecular structure of 1-tert-butyl 4-ethyl (2'R,3'R,5'R,2S,3S)-3-bromomethyl-3-hydroxy-2-[(2'-hydroxy-2',6',6'-trimethylbicyclo[3.1.1]hept-3'-ylidene)amino]succinate, C(21)H(34)BrNO(6), is presented.