Silylketenes under Kulinkovich conditions: alkene/ketene exchange versus nucleophilic addition. Application to the stereoselective preparation of vinylcyclopropanols |
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| Authors: | Eric RaponiJean-Marc Pons |
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| Affiliation: | Laboratoire de Réactivité en Synthèse Organique (RéSO), UMR-CNRS 6516, Faculté des Sciences et Techniques de Saint-Jérôme, 13397 Marseille Cedex 20, France |
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| Abstract: | Silylketenes react under Kulinkovich conditions through two competitive pathways: alkene/ketene exchange versus nucleophilic addition. In both cases, the organotitanium intermediate reacts with an aldehyde to yield an adduct which can undergo an elimination to yield a vinylcyclopropanol or an α,β-unsaturated carbonyl compound. |
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| Keywords: | silylketene low-valent titanium exchange aldehyde |
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