Asymmetric Trans-esterification of meso-2, 5-Dibromoadipate and Synthesis of Optically Active cis-2, 5-Disubstituted Pyrrolidines

Abstract

Asymmetric trans-esterification of meso-2, 5-dibromoadipate to ( - )-benzyl methyl 2, 5-dibromoadipate by lipase with subsequent chemical reactions afforded optically active cis-2, 5-disubstituted pyrrolidines. An equivalent asymmetric transformation was performed by selectively hydrolyzing a cis-2, 5-disubstituted pyrrolidine having a chiral N-substituent.