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.
| Original language | English |
|---|---|
| Pages (from-to) | 7811-7817 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 66 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - 16 Nov 2001 |
| Externally published | Yes |
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McCluskey, A., Muderawan, I. W., Muntari, & Young, D. J. (2001). A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic, and tetrapropargylic stannanes to carbonyl compounds. Journal of Organic Chemistry, 66(23), 7811-7817. https://doi.org/10.1021/jo015904x