Tetrahedron letters

Intermolecular aldol reactions via allylic o-stannyl ketyls

EJ Enholm, PE Whitley

Index: Enholm, Eric J.; Whitley, Paul E. Tetrahedron Letters, 1995 , vol. 36, # 50 p. 9157 - 9160

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Citation Number: 16

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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Intermolecular aldol reactions via allylic o-stannyl ketyls

Abstract

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