An acid-promoted pseudocine substitution manifold of γ-aminocyclopentenone enables divergent access to polycyclic indole derivatives

We demonstrated gamma-aminocyclopentenones to be a suitable surrogate for reactive cyclopentadienone via a pseudocine-substitution manifold. This approach enabled its orchestrated annulation with tailored bis-nucleophiles and to furnish complex beta,gamma-annulated cyclopentanoids or indole-based polycyclic architectures. This strategy represents a generalized means for direct, regioselective and stereoselective beta,gamma-functionalization of monosubstituted or unsubstituted aminocyclopentenones.

Automated summary

We demonstrated that gamma-aminocyclopentenones can serve as suitable substitutes for reactive cyclopentadienone via a pseudocine-substitution manifold. This approach allows for orchestrated annulation with specific bis-nucleophiles, leading to the synthesis of complex beta,gamma-annulated cyclopentanoids or indole-based polycyclic architectures. It represents a generalized method for the direct, regioselective, and stereoselective beta,gamma-functionalization of monosubstituted or unsubstituted aminocyclopentenones.