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| - A Highly Atom Efficient, Solvent Promoted Addition ofTetraallylic, Tetraallenic, and Tetrapropargylic Stannanes toCarbonyl Compounds
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| - Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes inmethanol to provide unsaturated alcohols in good to excellent yields (56−99%). These reactionsproceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation reactions also proceeded smoothly with reactive ketones such as ethylpyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethylacetals 4d and 4e are regiospecific with allylic rearrangement.
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