Table 2. Optimization of the Reaction Conditionsa.
| entry | catalyst | solvent | additive | t (days) | yield of 3aa (%)b | ee of 3aac |
|---|---|---|---|---|---|---|
| 1 | V | CH2Cl2 | 3 | 37 | 77 | |
| 2 | V | CHCl3 | 4 | 33 | 77 | |
| 3 | V | Cl CH2CH2Cl | 3 | 42 | 61 | |
| 4 | V | CCl4 | 3 | 49 | 49 | |
| 5 | V | Et2O | 2 | 43 | 64 | |
| 6 | V | toluene | 2 | 58 | 54 | |
| 7 | V | CH2Cl2 | MS (5 Å)d | 4 | 43 | 69 |
| 8 | V | CH2Cl2 | CF3CH2OHe | 4 | 47 | 69 |
| 9 | V | CH2Cl2 | K2CO3e | 3 | 39 | 0 |
| 10 | V | CH2Cl2 | PhCO2Hf | 5 | ||
| 11g | V | CH2Cl2 | 3 | 44 | 71 | |
| 12h | V | CH2Cl2 | 3 | 46 | 67 | |
| 13 | V | CH2Cl2 | 5 | 46 | 74 | |
| 14 | VI | CH2Cl2 | 4 | 52 | 76 | |
| 15 | VI | CH2Cl2 | 5 | 61 | 74 | |
| 16 | IX | CH2Cl2 | 3 | 51 | 74 | |
| 17 | IX | CH2Cl2 | 5 | 46 | 77 |
Reaction conditions: 0.1 mmol of 1a, 0.1 mmol of 2a, 5 mol % of catalyst in 1 mL of solvent at rt.
Isolated yield of 3aa.
Determined by chiral HPLC.
50 mg of MS 5 Å.
0.1 mmol of additive was used.
0.025 mmol of PhCO2H was used.
0.12 mmol of 1a.
0.12 mmol of 2a.
