Table 1 Initial reaction developmenta.
Entry | ligand | Solvent | Additiveb | Yield (%) | ee (%) |
|---|---|---|---|---|---|
1 | L1 | CH2Cl2 | - | 14 | 0 |
2 | L1 | PhMe | - | 79 | 0 |
3 | L1 | EtOAc | - | 97 | - |
4 | L1 | MeOH | - | 98 | 22 (R) |
5 | L1 | THF | - | 97 | 2 |
6 | L1 | TFE | - | 87 | 29 (S) |
7 | L2 | TFE | - | 70 | 18 (S) |
8 | L3 | TFE | - | 94 | 69 (S) |
9 | L4 | TFE | - | 80 | 86 (S) |
10 | L4 | TFE | I2 | 90 | 81 (S) |
11 | L4 | TFE | TsOH | 95 | 72 (S) |
12 | L4 | TFE | Et3N | 95 | 71 (S) |
13 | L4 | TFE | NaBF4 | 92 | 56 (S) |
14 | L4 | TFE | FeCl3 | 88 | 89 (S) |
15 | L4 | TFE | CsCl | 78 | 86 (S) |
16 | L4 | TFE/MeOAc | FeCl3 | 96 | 97 (S) |
17c | L4 | TFE/MeOAc | HCl | 96 | 95 (S) |
18d | L4 | TFE/MeOAc | FeCl3 | 99 | 98 (S) |
19e | L4 | TFE/MeOAc | FeCl3 | 88 | 95 (S) |
