Intermolecular aldol reactions via allylic o-stannyl ketyls

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 whi...

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Bibliographic Details
Published in:Tetrahedron letters 1995-12, Vol.36 (50), p.9157-9160
Main Authors: Enholm, Eric J., Whitley, Paul E.
Format: Article
Language:English
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)01999-X