Catalytic Enantioselective Alkylation of Aldehydes with 3-Bromooxindoles

作者：Zhen Li, Xiao‐Ming Zhang, Fu‐Min Zhang, Yong‐Qiang Tu · 发表于：Organic Letters · 年份：2023 · DOI：10.1021/acs.orglett.3c02882 · 被引用次数：14 · 研究领域：Asymmetric Synthesis and Catalysis、Alkaloids: synthesis and pharmacology、Chemical synthesis and alkaloids

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 β-aldehyde appendages. Further application of this synthetic methodology enables the construction of the tricyclic cores of akuammiline-type alkaloids.