Table 3. Effect of Different Catalyst Substituents on the Yield of the Ring-Opening Reaction and ee of the Products.
| entry | catalyst | solvent | temp (°C) | time (h) | yield (%)a | head (%)b,c |
|---|---|---|---|---|---|---|
| 1 | 1j | toluene | –30 | 24 | 87 | 30 |
| 2 | 1m | toluene | –30 | 24 | 98 | 92 |
| 3 | 1o | toluene | –30 | 24 | 87 | 30 |
| 4 | 1n | toluene | –30 | 24 | 82 | 13 |
| 5 | 1o | toluene | –30 | 24 | 83 | 6 |
| 6 | 1o | toluene | –30 | 24 | 83 | 33 |
| 7 | 1p | toluene | –30 | 24 | 87 | 30 |
| 8 | 1q | toluene | –30 | 24 | 85 | 17 |
| 9 | 1r | toluene | –30 | 24 | 87 | 6 |
| 10 | 1s | toluene | –30 | 24 | 87 | 60 |
| 11 | 1a | toluene | –30 | 24 | 90 | 12 |
| 12 | 1t | toluene | –30 | 24 | 90 | 25 |
| 13 | 1m | CH2Cl2 | –30 | 24 | 90 | 69 |
| 14 | 1m | hexane | –30 | 24 | 93 | 49 |
| 15 | 1m | toluene/CCl4 | –30 | 24 | 84 | 27 |
| 16 | 1m | THF | –30 | 24 | 84 | 27 |
| 17 | 1m | diethyl ether | –30 | 24 | 85 | 29 |
Isolated yield of products.
Determined by GC using the Agilent HP-1 column (19091Z-413, 30 m × 0.32 mm × 0.25 μm); conditions: initial temp, 50 °C; initial time, 3 min; 25.0 °C/min; final temp, 280 °C; 17 psi; retention time, 10.76 14.12 min.
Absolute configuration.8