Table 1 Optimization of reaction conditions
| |||||
---|---|---|---|---|---|
Entry | Catalyst | Solvent | Yield (%) | dr | ee (%) |
1 | 4a | CH2Cl2 | 99 |  > 20:1 | 97 |
2 | 4b | CH2Cl2 | 95 | 14:1 | –97 |
3 | 4c | CH2Cl2 |  < 1 | — | — |
4 | 4d | CH2Cl2 | 89 | 14:1 | –92 |
5 | 4e | CH2Cl2 | 69 | 17:1 | –94 |
6 | 4f | CH2Cl2 | 72 | 11:1 | 93 |
7 | 4g | CH2Cl2 | 82 | 10:1 | 94 |
8a | 4a | CH2Cl2 | 84 |  > 20:1 | 97 |
9b | 4a | CH2Cl2 | 14 |  > 20:1 | 97 |
10 | 4a | CHCl3 | 93 |  > 20:1 | 97 |
11 | 4a | Benzene | 93 |  > 20:1 | 95 |
12 | 4a | Toluene | 90 |  > 20:1 | 95 |
13 | 4a | Et2O | 59 | 20:1 | 93 |
14 | 4a | THF | 15 | 20:1 | 96 |
15 | 4a | EtOAc | 38 | 17:1 | 94 |
16 | 4a | CH3CN | 54 | 3.6:1 | 95 (93d) |
17 | 4a | EtOH | 23 | 9.2:1 | 96 (88d) |
18c | 4a | CH2Cl2 | 84 |  > 20:1 | 96 |