Table 2.
Scope of the reaction of the allene 1a with various sulfonamide 2.a
| |||||
|---|---|---|---|---|---|
| Entry | R | Time (h) | 3 | Yield (%)b | E/Zc |
| 1 | H | 12 | 3a | 95 | 93:7 |
| 2 | 4-Me | 12 | 3b | 96 | 93:7 |
| 3 | 4-MeO | 24 | 3c | 93 | 94:6 |
| 4 | 4-Br | 12 | 3d | 95 | 94:6 |
| 5 | 4-Cl | 9 | 3e | 96 | 93:7 |
| 6 | 4-F | 7 | 3f | 98 | 94:6 |
| 7 | 4-NO2 | 30 | 3g | 92 | 90:10 |
| 8 | 3-Me | 10 | 3h | 95 | 94:6 |
| 9 | 3-Br | 8 | 3i | 93 | 93:7 |
| 10 | 3-Cl | 9 | 3j | 88 | 96:4 |
| 11 | 3-NO2 | 24 | 3k | 88 | 89:11 |
| 12 | 2-NO2 | 26 | 3l | 82 | 99:1 |
| 13 | 2-Me | 16 | 3m | 94 | 91:9 |
| 14 | 2-Cl | 10 | 3n | 97 | 96:4 |
| 15 | 2-F | 9 | 3o | 96 | 91:9 |
| 16 | 2-CO2Me | 24 | 3p | 92 | 94:6 |
| 17 | 2,6-di-Cl | 8 | 3q | 91 | 95:5 |
| 18 |
![]() (2r) |
8 | 3r | 81 | 93:7 |
Reactions of 1a (0.3 mmol) and 2 (0.2 mmol) were performed in Et2O (2 mL) at room temperature.
Isolated yield based on 2.
Determined using 1H NMR spectroscopy.
