Reaction scope of different allylic alcohols and aminea.
| ||||||
|---|---|---|---|---|---|---|
| Entry | Allylic alcohols | Nucleophine | T (°C) | Time (h) | Product | Yieldb (%) |
| 1 |
|
|
30 | 1.5 | 6a | 91 |
| 2 | 4a |
|
30 | 4 | 6b | 91 |
| 3 | 4a |
|
30 | 1.5 | 6c | 81 |
| 4c | 4a |
|
50 | 26 | 6d | 77 |
| 5 | 4a | CH3SO2NH25e | 50 | 7.5 | 6e | 86 |
| 6c | 4a | CbzNH25f | 30 | 2 | 6f | 98 |
| 7c | 4a |
|
50 | 26 | 6g | 93 |
| 8 | 4a |
|
30 | 12 | 6h | 98 |
| 9 |
|
5a | 85 | 53 | 6i, 6i′ | 51 (2 : 1)d |
| 10 | 4b | 5b | 85 | 53 | 6j, 6j′ | 48 (3 : 1)d |
| 11 |
|
5a | 50 | 25 | 6k | 48 |
| 12 | 4c | 5b | 50 | 25 | 6l | 42 |
| 13 |
|
5a | 50 | 8 | 6m | 56 |
| 14 | 4d | 5b | 50 | 9 | 6n | 70 |
Reaction conditions: 1 mmol allylic alcohols, 2 mmol nucleophile, 3d (0.05 mol% Au), 0.05 mol% AgOTf, 2 mL dioxane, argon atmosphere.
Isolated yield.
0.2 mol% 3d, 0.2 mol% AgOTf.
The ratio of α-product to γ-product.