Organocatalytic domino sequence to asymmetrically access spirocyclic oxindole-α-methylene-γ-lactams

An asymmetric allylic alkylation-lactamization domino sequence of 3-aminooxindoles with Morita-Baylis-Hillman carbonates catalyzed by quinidine derivative (beta-ICD) was developed. And a series of chiral spirocyclic oxindole-alpha-methylene-gamma-lactams have been facilely prepared in good yields and stereoselectivities. This developed protocol would broaden the utilization of Morita-Baylis-Hillman carbonates in asymmetric construction of spirocyclic oxindoles. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

A new synthetic method has been developed for the efficient synthesis of chiral spirocyclic oxindole-alpha-methylene-gamma-lactams. The method utilizes Morita-Baylis-Hillman carbonates as substrates and quinidine derivatives as catalysts to achieve stereoselective control over the products. This research broadens the application of Morita-Baylis-Hillman carbonates in the asymmetric construction of spirocyclic oxindoles.