Direct versatile route to conformationally constrained glutamate analogues

Abstract

Novel conformationally constrained glutamate analogues are readily available from (S)-pyroglutamic acid; using a bicyclic lactam template, diastereocontrolled and sequential modification of the pyrrolidine ring is possible, allowing a versatile access to several glutamate and kainoid analogues; variations in the C(2)H–C(3)H coupling constants were observed depending upon the nature of remote substituents on the heterocyclic ring, consistent with modification of the ring conformation.