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Abstract
The direct vinylogous aldol reaction of α-substituted α,β-unsaturated aldehydes with
isatins is described. The chemistry provides easy access to valuable 3-substituted
3-hydroxyoxindole derivatives with high stereocontrol and perfect γ-site selectivity.
Preliminary mechanistic studies suggest that, depending on the nature of the α-branched
enal substituents, two divergent reaction mechanisms can be operating, leading to
different products and stereochemical outcomes.