Catalytic Enantioselective Alkylation of Aldehydes with 3-Bromooxindoles

Organic Letters
2023.0

Abstract

An asymmetric conjugate addition of aldehydes with o-azaxylylene intermediates (indol-2-ones) from 3-bromooxindoles has been developed. The use of a novel spiro-pyrrolidine (SPD)-derived bifunctional N-sulfonylated amide catalyst is essential for a highly diastereo- and enantioselective transformation to provide a wide array of enantioenriched C3 quaternary oxindoles with structurally diverse beta-aldehyde appendages. Further application of this synthetic methodology enables the construction of the tricyclic cores of akuammiline-type alkaloids.

Knowledge Graph

Similar Paper