Synthese der enantiomeren 2‐Pyrrolidinessigsäuren

Abstract

Synthesis of the enantiomeric 2‐pyrrolidineacetic acids. Starting from the enantiomeric Z‐prolines ( 1 ) the title compounds 9 were prepared in optically pure form by using the Arndt‐Eistert process. It could be shown by chemical correlation that the stereochemical determining step of the reaction sequence, the Wolff rearrangement of the N‐acylated diazomethyl ketones 5 , proceeds with strict retention of configuration. Some known chiroptical methods for determination of absolute configuration were applied to the target compounds.