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

DOI: 10.1016/0040-4039(95)02260-0

Source and publish data:

Tetrahedron Letters p. 559 - 562 (1996)

Update date:2022-08-06

Topics:

Authors:

Enholm, Eric J.

Whitley, Paul E.

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Article abstract of DOI:10.1016/0040-4039(95)02260-0

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 halides and HMPA to provide a useful and mild alternative to analogues Li-NH₃ alkylations.

Full text of DOI:10.1016/0040-4039(95)02260-0

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