Abstract
A mild and neutral free radical reaction of an α,β-unsaturated ketone and tributyltin radical produced a resonance-stabilized allylic O-stannyl ketyl intermediate. A tin(IV) enolate, produced by subsequent hydrogen atom transfer, was next quenched with various aldehydes to yield an aldol product which was readily eliminated with p-toluenesulfonic acid to afford new α,β-unsaturated ketones with E/Z ratios up to > 100:1.
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