Sequential nucleophilic addition/1,2-rearrangement of N-iminolactam: A ring-contractive strategy for the synthesis of 2-acyl pyrrolidines

A sequential nucleophilic addition/ring contraction of alpha-bromo N-iminolactam with organometallic reagents for the synthesis of 2-acyl pyrrolidines has been developed. The reaction allows facial construction of 2-acyl pyrrolidines incorporating not only aryl and heteroaryl groups, but alkenyl, alkynyl, and alkyl groups. Moreover, 2-acyl pyrrolidine products can be further transformed into the pyrrolidinyl alcohol, epoxide, b-lactam, and pyrazole. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

A new method for synthesizing 2-acyl pyrrolidines has been developed through sequential nucleophilic addition/ring contraction of alpha-bromo N-iminolactam with organometallic reagents. This reaction allows the incorporation of various groups, including aryl, heteroaryl, alkenyl, alkynyl, and alkyl groups, into the facial construction of 2-acyl pyrrolidines. Moreover, the 2-acyl pyrrolidine products can be further transformed into different compounds such as pyrrolidinyl alcohol, epoxide, b-lactam, and pyrazole.