Table 2.
One-pot synthesis of α-substituted ketones via tandem allylic substitution/oxidation.
| |||||
|---|---|---|---|---|---|
| Entry | Allyl acetate | α-Substituted ketones | Yield (%)[a] | ||
| 1 | 1a |
|
3a | 85 | |
| 2 | 1a |
|
3b | 82 | |
| 3 | 1a |
|
3c | 81 | |
| 4 | 1a |
|
3d | 75 | |
| 5 | 1f |
|
|
3e | 65 |
| 6 | 1f | 3e | 78[b] | ||
Yield of purified and isolated products.
Allylic substitution carried out with Pd(OAc)2 (5 mol %) and PPh3 (10 mol %) at rt, and oxidation carried out with 3 equiv of NaBO3·H2O in THF/H2O (1:1) at rt.