Abstract

Spiroannulation of oxindole-3-oxy acrylates with ynones involving two overlapping, base differentiated cascades has been observed. Initial exposure of ynones and oxindole 3-oxy acrylates to K2CO3 triggered a tandem Michael-Michael cascade to deliver a pair of spiroannulated diastereomers. Further exposure to LiHMDS led to deep restructuring through a second multistep cascade involving stereoselective recreation of the C3 quaternary center to furnish 3H-spiro[furan-2,3'-indolin]-2'-ones with functional amplification and scrambling. This new scaffold can be directly accessed in a one-flask operation from ynones and oxindole-3-oxy acrylates.

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