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

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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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2026-07-01
DOI
https://doi.org/10.1002/adsc.70503
Primary Topic
Synthesis and Reactivity of Heterocycles
Type
article
Field-Weighted Citation Impact
0.00
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article

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

Jun-Hao Shen, Xing‐Wang Wang, Bailin Wang, Wei‐Tai Fan et al.
Advanced Synthesis & Catalysis
Synthesis and Reactivity of Heterocycles
article

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

Jun-Hao Shen, Xing‐Wang Wang, Bailin Wang, Wei‐Tai Fan, Huang‐Jie Zhou, Yan‐Qi Ma
article en

Abstract

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.

Advanced Synthesis & CatalysisVol. 368(13)
Zhengzhou University (CN), Soochow University (CN), Zhengzhou University of Science and Technology (CN)
Openalex Percentile: Top 13%
Synthesis and Reactivity of Heterocycles
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Chiral Thiourea and Rare‐Earth Lewis Acid Successively Catalyzed Asymmetric Michael/Double Friedel–Crafts Reactions for Optically Active Indolyl‐Substituted Spirooxindole‐Hydroindolizine Backbones — Jun-Hao Shen, Xing‐Wang Wang, et al. · Advanced Synthesis & Catalysis (2026) | TGRS Research Map | TGRS