Tin(IV) enolates from allylic O-stannyl ketyls: Reactions with alkyl halides and HMPA

The mild free radical reaction of an α,β-unsaturated ketone and tributyltin radical produced a resonance-stabilized allylic O-stannyl ketyl intermediate. A subsequent hydrogen atom transfer produced a tin(IV) enolate which reacts readily with activated alkyl halides and HMPA to provide a useful and...

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Bibliographic Details
Published in:Tetrahedron letters 1996-01, Vol.37 (5), p.559-562
Main Authors: Enholm, Eric J., Whitley, Paul E.
Format: Article
Language:English
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Summary:The mild free radical reaction of an α,β-unsaturated ketone and tributyltin radical produced a resonance-stabilized allylic O-stannyl ketyl intermediate. A subsequent hydrogen atom transfer produced a tin(IV) enolate which reacts readily with activated alkyl halides and HMPA to provide a useful and mild alternative to analogous LiNH 3 alkylations. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)02260-0