Chiral Phosphine Catalyzed Allylic Alkylation of Benzylidene Succinimides with Morita-Baylis-Hillman Carbonates.

ABSTRACT: Owing to their unique chemical properties, α-alkylidene succinimides generally act as versatile synthons in organic synthesis. Compared with well-established annulations, nucleophilic alkylations of α-alkylidene succinimides are very limited. Accordingly, an organocatalytic allylic alkylation of α-benzylidene succinimides with Morita-Baylis-Hillman (MBH) carbonates was established. In the presence of a chiral phosphine catalyst, α-benzylidene succinimides reacted smoothly with MBH carbonates under mild conditions to furnish a series of optical active succinimides in high yields and enantioselectivities. Different from the reported results, the organocatalytic enantioselective construction of pyrrolidine-2,5-dione frameworks bearing contiguous chiral tertiary carbon centers was achieved via

SUBMITTER: Liu C 

PROVIDER: S-EPMC10053092 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature