Enantioselective Tandem Michael Addition and Cyclization Reaction Enabled by Dual Organo/Copper Catalysis: Access to Functionalized 4 H -Pyrans
Abstract
An enantioselective (3 + 3) annulation between 1,3-nitroenynes and α-cyano ketones has been developed using a cooperative organo/copper dual catalytic system. The transformation proceeds through an enantioselective Michael addition catalyzed by the synergistic effect of an organocatalyst and metal–ligand complex, followed by Lewis-acid-catalyzed annulation, furnishing pentasubstituted 4 H -pyran derivatives in good yields and good to excellent enantioselectivities. Mechanistic investigations were conducted to elucidate the reaction pathway, and its practical applicability was demonstrated through a scale-up reaction and versatile post synthetic modifications.
Fields of Study & Subjects
Synthesis of heterocyclic compounds
Catalytic Alkyne Reactions
Asymmetric Synthesis and Catalysis
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 4
- Pages
- 1235–1240
- Publication date
- 16 January 2026
- Language
- EN