Table 1.
Ireland–Claisen rearrangement of 1a–c with LDA as the base without organocatalysts.
| Entry | R | R’3SiX (equiv) | Temperature (°C) | Time (h) | Yield of 2 (%) | dr |
| 1 | H | Me3SiCl (1.1) | rt | 168 | 63 | – |
| 2 | H | Me3SiCl (1.1) | 66 | 3 | 41 | – |
| 3 | Me | Me3SiCl (1.1) | rt | 72 | 42 | 76:24 |
| 4 | Me | Me3SiCl (1.1) | 66 | 2 | 36 | 76:24 |
| 5 | Me | Me3SiCl (1.1) | rt | 20 | 38 | 77:23 |
| 6 | Me | – | rt | 20 | 30 | 79:21 |
| 7 | Ph | Me3SiCl (1.0) | rt | 168 | 0 | – |
| 8 | Ph | t-BuMe2SiOTf (1.1) | rt | 168 | 0 | – |