Spirooxindoles

Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis

“…Not surprisingly, organocascade reactions were successfully used for the stereoselective preparation of valuable spirocyclic compounds, 4 for example, the privileged scaffold�spirocyclic oxindole derivatives (spirooxindoles). 5 The spirooxindole structural motif appears as part of various natural or synthetic compounds with remarkable biological activity, including medicinally relevant compounds (Figure 1). 6 Organocascade reactions initiated by the Michael reaction are highly efficient for the construction of spirooxindole-fused derivatives, 7 using either oxindoles with nucleophilic C3 (Michael donors) 8−10 or electrophilic methyleneindolinones (Michael acceptors).…”

Exploring Regio- and Stereoselectivity in [3+2] Cycloaddition: Molecular Electron Density Theory Approach for Novel Spirooxindole-Based Benzimidazole with Pyridine Spacer

“…Several synthetic approaches have the ability to access spirooxindoles; among them are the use of nano-catalysis [29], organocatalyst oxidative annulations [30][31][32][33], microwave irradiations [34], sonochemical strategy [35], NHC (N-Heterocyclic carbene) catalyst-mediated [3+2] cycloaddition annulation [36], and transition metal catalysts [37,38] (e.g., Ru, Rh, Pd, etc.) that require a specific olefin or indolinone-based alkene moiety in the precursor structure.…”

Sequential organo and metal catalyzed reaction between 3-pyrrolyloxindoles and linear nitroenynes: access to cyclic aza-spirooxindoles

“…Many different natural compounds and drug molecules possess structural frameworks that contain spirooxindole. 1 In particular, the aza-spirooxindole unit has been frequently found in several bioactive natural products. 2 For instance, one form of Aspidosperma alkaloid is (−)-vincatine.…”

“…6 Thus, the stereoselective preparation of functionalized aza-spirooxindole scaffolds has received a lot of attention in recent years. 1 However, the majority of the techniques centred on the formal [3+2] cyclizations for the effective access to spiropyrrolidine oxindoles. 7 In contrary, less focus was paid to developing an asymmetric process for creating spiropiperidinyl oxindole.…”