A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic, and tetrapropargylic stannanes to carbonyl compounds. |
| |
| Authors: | A McCluskey I W Muderawan Young" target="_blank">D J MuntariYoung |
| |
| Institution: | Chemistry, School of Biological and Chemical Sciences, The University of Newcastle, University Drive, Callaghan, NSW 2308, Australia. amcclusk@mail.newcastle.edu.au |
| |
| 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. |
| |
| Keywords: | |
|
|
