Rapid diastereocontrolled synthesis of 2,2,5-trisubstituted pyrrolidines

Abstract

2,2,5-Trisubstituted pyrrolidines are available from allylic pyroglutamates by Ireland–Claisen ester rearrangement followed by Eschenmoser sulfide contraction and reduction in a highly diastereoselective and efficient sequence. Some of the products from this sequence exhibit activity against S. aureus, but are much less active against E. coli.