Efficient Assembly of Cyclohexane‐Tethered Bispirooxindoles via Carboanion Relay Enabled [1 + 2 + 2 + 1] Annulation

Comprehensive Summary A novel carboanion relay enabled [1 + 2 + 2 + 1] cascade cyclization reaction utilizing rarely used isatin‐derived β ‐silylcarbinols and aryl methyl ketones as readily available starting materials has been developed, endowing a powerful platform for the streamline synthesis of cyclohexane‐tethered bispirooxindoles in decent yields with high diastereoselectivities. This protocol was realized by merging triple Michael additions and C—C bond cleavage using Cs 2 CO 3 as a robust promotor under transition metal‐free conditions. The practicability of this method is demonstrated by its simple operation, broad substrate scope as well as easy scale‐up.