Table 1 Optimization of the reaction conditionsa
From: Chiral phosphoric acid catalyzed aminative dearomatization of α-naphthols/Michael addition sequence
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|---|---|---|---|---|---|---|
Entry | C | Solvent | Temperature (°C) | Time (h) | Yield (%)b | ee (%)c |
1 | C1 | DCE | 50 | 24 | 85 | 75 |
2 | C2 | DCE | 50 | 24 | 90 | 99 |
3 | C3 | DCE | 50 | 24 | 87 | 63 |
4 | C4 | DCE | 50 | 24 | 90 | 98 |
5 | C5 | DCE | 50 | 24 | 85 | 57 |
6 | C6 | DCE | 50 | 24 | 83 | 2 |
7 | C7 | DCE | 50 | 24 | 83 | 59 |
8 | C2 | EtOAc | 50 | 24 | 86 | 97 |
9 | C2 | THF | 50 | 24 | 85 | 96 |
10 | C2 | toluene | 50 | 24 | 87 | 98 |
11 | C2 | DCE | 40 | 36 | 88 | 99 |
12 | C2 | DCE | 60 | 12 | 85 | 99 |
13d | C2 | DCE | 50 | 36 | 77 | 99 |
14e | C2 | DCE | 50 | 96 | 81 | 99 |
15e | C2 | DCE | 80 | 30 | 81 | 99 |
16f | C2 | DCE | 80 | 24 | 69 | 98 |
17g | C2 | DCE | 80 | 24 | 52 | 97 |
18 | / | DCE | 50 | 12 | complex | N.D. |
