Abstract
We have explored the addition of tetraallylstannane (7) to a variety of N-protected Weinreb amides (N-phthalimido and N-benzyl). Reactions were conducted in methanol and the ionic liquid, butylmethylimidazole tetrafluoroborate (bmim[BF4]), yields of the corresponding N-protected allylketones were moderate to good. Allylation of the corresponding aminoaldehydes gave excellent yields of homoallylic alcohols (68-94%) and moderate to good diastereoselectivities (50-86%).
| Original language | English |
|---|---|
| Pages (from-to) | 8147-8151 |
| Number of pages | 5 |
| Journal | Tetrahedron Letters |
| Volume | 41 |
| Issue number | 42 |
| DOIs | |
| Publication status | Published - 14 Oct 2000 |
| Externally published | Yes |
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McCluskey, A., Garner, J., Young, D. J., & Caballero, S. (2000). Tetraallylstannane and Weinreb amides: A simple 'green' route to N-protected homoallylic alcohols and allyl ketones. Tetrahedron Letters, 41(42), 8147-8151. https://doi.org/10.1016/S0040-4039(00)01408-8