title: A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic, and tetrapropargylic stannanes to carbonyl compounds.
abstract: Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed 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 ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.
authors.affiliation: Chemistry, School of Biological and Chemical Sciences, The University of Newcastle, University Drive, Callaghan, NSW 2308, Australia. amcclusk@mail.newcastle.edu.au
authors.forename: A
authors.initials: A
authors.lastname: McCluskey
authors.forename: I W
authors.initials: IW
authors.lastname: Muderawan
authors.lastname: Muntari
authors.forename: D J
authors.initials: DJ
authors.lastname: Young