Table 1. Screen of 3,3′-Substituted BINOL Ligands for the Enantioselective para-Claisen Rearrangement of Illicinole (3).
| entry | R | temperature | er of 2 |
|---|---|---|---|
| 1 | H | rt | 46:54 |
| 2 | Me | rt | 45:55 |
| 3 | Ph | rt | 40:60 |
| 4 | SiPh3 | rt | 57:43 |
| 5 | 2,6-dimethylphenyl | rt | 40:60 |
| 6 | 1-naphthyl | rt | 40:60 |
| 7 | 9-anthracenyl | rt | 30:70 |
| 8 | 9-anthracenyl | –40 °C | 26:74 |
| 9 | 9-anthracenyl | –60 °C | nr |
| 10 | neopentyl | rt | 76:24 |
| 11 | neopentyl | –40 °C | 87:13 |
| 12 | neopentyl | –60 °C | nr |
| 13 | methylene-1-adamantyl | –20 °C | 84:16 |
| 14 | methylene-1-adamantyl | –40 °C | nr |
