Dual Cu/Ir Catalyzed Asymmetric Allylation and Pictet-Spengler Cyclization: Stereodivergent Access to Chiral Indole Fused 9-Azabicyclo[4.2.1]nonanes
Xin-Lian Liu , Lu Xiao , Yi Liu , Yan Li , Zuo-Fei Wang , Xin Chang , Xiu-Qin Dong , Chun-Jiang Wang
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (11) : 1223 -1229.
Dual Cu/Ir Catalyzed Asymmetric Allylation and Pictet-Spengler Cyclization: Stereodivergent Access to Chiral Indole Fused 9-Azabicyclo[4.2.1]nonanes
Nitrogen-containing bridged-heterocycles and indoles are key subunits of many natural products and pharmacologically active molecules. We herein present a bimetallic Cu/Ir catalyzed asymmetric allylation of ketimine esters and (E)-4-indolyl allyl carbonates followed by acid-promoted Pictet-Spengler cyclization sequences, enabling stereodivergent synthesis of chiral indole fused 9-azabicyclo[4.2.1]nonanes containing an eight-membered ring with one tertiary and two quaternary stereogenic centers. This one-pot sequential protocol features step economy, good substrate tolerance, and excellent stereoselective control.
Asymmetric catalysis / Synergistic catalysis / Stereodivergent synthesis / Pictet-Spengler cyclization / Azomethine ylides / Medium-ring compounds
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
/
| 〈 |
|
〉 |
PDF
