Asymmetric Inverse-Electron-Demand Diels–Alder Reaction of 2-Pyrones with Acyclic Indolyl Alkenes for the Synthesis of Chiral N -Alkylindoles
Abstract
For the first time, this study employed a series of acyclic indolyl alkenes as dienophiles and successfully developed their inverse-electron-demand Diels–Alder (IEDDA) reactions with 2-pyrones, thereby constructing chiral N -alkylindole compounds bearing four chiral carbon centers. With an easily accessible BOX ligand, we achieved Zn-catalyzed IEDDA reactions of N -vinyl indoles and N -alkenyl indoles with 2-pyrones. Alternatively, under copper catalysis, the IEDDA reactions of N -styryl indoles with 2-pyrones were also developed. All reactions exhibited excellent regioselectivity (only one isomer), diastereoselectivity (dr >95:5), and enantioselectivity (up to 99% ee).
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Asymmetric Synthesis and Catalysis
Axial and Atropisomeric Chirality Synthesis
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 9
- Pages
- 3033–3038
- Publication date
- 18 February 2026
- Language
- EN