Transaminase-Triggered Synthesis of 2,5-Disubstituted Pyrrolidines

Abstract

2,5-Disubstituted pyrrolidines were synthesised from ketoenone substrates using a transaminase-triggered intramolecular aza-Michael reaction in moderate to good yields. The pyrrolidines were isolated as mixtures of diastereoisomers and a novel epimerisation was developed to isolate cis-2,5-N-nosyl-protected pyrrolidines as the major product in all examples, apart from the ester derivative, with high levels of diastereoselectivity and moderate yields.