Tetrahedron Letters p. 9157 - 9160 (1995)
Update date:2022-08-05
Topics:
Enholm, Eric J.
Whitley, Paul E.
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 transver, 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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Doi:10.1071/CH9951917
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(1996)
