PPh 3 -Promoted Remote ε′,ε′-Regioselective (4 + 1) Annulation of Pyrrolidinone-Based MBH Carbonates with 1-Heterodienes to Access Highly Substituted 1,6-Diazaspiro[4.4]nonenes
Abstract
An efficient and remote ε′,ε′-regioselective (4 + 1) annulation reaction between pyrrolidinone-based Morita–Baylis–Hillman (MBH) carbonates and 1-heterodienes was pioneered in the presence of triphenylphosphine (PPh 3 ). This approach enables the facile synthesis of a wide variety of highly substituted 1,6-diazaspiro[4.4]nonenes bearing bis-N-substituted quaternary carbon centers, achieving high yields (up to 90%) along with excellent regioselectivities. Moreover, the practical applicability of this methodology is substantiated by its successful implementation in subsequent synthetic transformations and the late-stage functionalization of drug molecules. Additionally, a molecular docking study was carried out to explore the potential biological activities of the synthesized products.
Fields of Study & Subjects
Cyclopropane Reaction Mechanisms
Catalytic C–H Functionalization Methods
Synthesis of heterocyclic compounds
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 24
- Pages
- 7576–7580
- Publication date
- 5 June 2026
- Language
- EN