Enantioselective Construction of Spirocyclohexadienones Via NHC-Catalyzed Formal [5 + 1] Annulation Reaction of Dienals
Abstract
The utilization of the NHC-catalyst remote LUMO activation intermediate for the construction of structurally diverse spirooxindole derivatives remains unexplored. Herein, we reported the NHC-catalyzed asymmetric 1,6-cycloaddition reaction of α,β-γ,δ-unsaturated aldehyde with 2-sulfonamidoindolines. These reactions involve H-transfer and tautomerization as the key catalytic process and enable facile access to various spirocyclohexadienone-fused 2-sulfonamidoindolines, giving the spirocyclic products in moderate to excellent yields with good to excellent enantioselectivities. These procedures may provide alternative synthetic strategy for the enrichment of spirooxindoles.
Fields of Study & Subjects
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Synthetic Organic Chemistry Methods
Asymmetric Synthesis and Catalysis
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 31
- Pages
- 10045–10050
- Publication date
- 25 July 2026
- Language
- EN