Table 1. Optimization of reaction conditions.
Entry | Cu catal. | Organocatal. | Additive | Yield (%)* | ee %† |
1 | CuOTf | C1 | – | (84)‡ | – |
2 | CuOTf | C2 | – | (76)§ | – |
3 | CuOTf | A1 | – | 47 | 63 |
4 | CuOTf | A1 | P1 | 52 | 91|| |
5 | CuOTf | A2 | P1 | 52 | 76|| |
6 | CuOTf | A3 | P1 | 74 | 84|| |
7 | CuOTf | A4 | P1 | 65 | 93|| |
8 | CuOTf | A5 | P1 | 73 | 89|| |
9 | CuOTf | A6 | P1 | 53 | 87|| |
10 | CuOTf | A4 | P2 | 31 | 73|| |
11 | CuOTf | A4 | P3 | 81 | 73|| |
12 | CuOTf | A4 | P4 | 67 | 63|| |
13 | CuOTf | A4 | P1 | 76 | 93 |
14 | (CuOTf)2•toluene | A4 | P1 | 78 | 93 |
15 | (CuOTf)2 | A4 | P1 | 70 | 92 |
16 | (CuOTf)4PF6 | A4 | P1 | 77 | 93 |
17 | CUBr | A4 | P1 | (87)¶ | – |
*Determined by GC using n-dodecane as an internal standard.
†Determined by chiral high-performance liquid chromatography.
‡The imine intermediate obtained in 84% yield.
§The imine intermediate obtained in 76% yield.
||Twenty mole percent of additive was used.
¶The imine intermediate obtained in 87% yield.