An efficient organocatalytic asymmetric Friedel‐Crafts alkylation/N‐hemiacetalization reaction of 2‐aminoindoles with α,β‐unsaturated aldehydes was developed. By incorporating an amino group at the C2 position of indole, the nucleophilicity of the C3… Click to show full abstract
An efficient organocatalytic asymmetric Friedel‐Crafts alkylation/N‐hemiacetalization reaction of 2‐aminoindoles with α,β‐unsaturated aldehydes was developed. By incorporating an amino group at the C2 position of indole, the nucleophilicity of the C3 position of indole and the amino group were leveraged to generate an enamine‐type ternary synthon. This approach enabled the construction of a range of chiral tetrahydro‐α‐carboline skeletons with potential biological activity, delivering moderate to excellent yields (46‐83%) and achieving outstanding enantioselectivity (up to 99% ee).
Journal Title: European Journal of Organic Chemistry
Year Published: 2025
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!