An organobase‐controlled, divergent cascade reaction to construct spirocyclohexene indane‐1,3‐diones and coumarin‐fused cyclopentanes is reported. The cascade reaction is triggered by the 1,6‐addition of 3‐homoacylcoumarins to the indanedione‐derived acceptors and further regio/chemoselective reaction that preferentially resulted in spiro systems and fused cyclopentanes in a diversity‐oriented manner. The 1,6‐addition/aldol and 1,6‐addition/vinylogous Michael addition cascade processes were controlled by different base/solvent systems to the predominant formation of one of the two carbocyclic compounds.magnified image
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