Table 2. Optimization of the reaction conditionsa.
| |||||
|---|---|---|---|---|---|
| Entry | 1 | Cat. | Yield (%)b | ee (%)c | drd |
| 1 | 1a | — | 29 | 0 | 1.5 : 1 |
| 2 | 1v | — | 32 | 0 | 10 : 1 |
| 3 | 1a | C6 | 83 | 0 | 1.2 : 1 |
| 4 | 1v | C6 | 80 | 2 | 10 : 1 |
| 5 | 1v | CP1 | 79 | 44 | 11.5 : 1 |
| 6 | 1v | CP2 | 72 | 7 | 9 : 1 |
| 7 | 1v | CP3 | 82 | 63 | 7 : 1 |
| 8 | 1v | CP4 | 74 | 47 | 4.5 : 1 |
| 9 | 1v | CP5 | 77 | 83 | 4 : 1 |
Reaction conditions: 1v (0.025 mmol), 4a (0.025 mmol), catalyst (10 mol%) in toluene (0.25 mL), and 5 Å MS(25 mg) at 0 °C for 3 h.
Isolated yield.
ee determined by chiral HPLC analysis.
dr determined by crude 1H NMR analysis.