DOI: 10.1002/adsc.70503 ISSN: 1615-4150

Chiral Thiourea and Rare‐Earth Lewis Acid Successively Catalyzed Asymmetric Michael/Double Friedel–Crafts Reactions for Optically Active Indolyl‐Substituted Spirooxindole‐Hydroindolizine Backbones

Bai‐Lin Wang, Yan‐Qi Ma, Huang‐Jie Zhou, Jun‐Hao Shen, Wei‐Tai Fan, Xing‐Wang Wang

A successive Michael/double Friedel–Crafts cascade reaction of ( E )‐2‐hydroxyaryl‐2‐oxobut‐3‐enoates, 3‐pyrrolyloxindoles, and indole or its derivatives was reported. The three‐step process was catalyzed by the combination of a chiral thiourea catalyst and a rare‐earth Lewis acid catalyst. Indolyl‐substituted spirooxindole‐hydroindolizines bearing two quaternary and one tertiary stereogenic centers were obtained in high yields with excellent diastereo‐ and enantioselectivity.

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