Table 1.
Optimization of the reaction conditions
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Entry | Rh catalysta | Base | Solvent | Temp. | Yield | ee |
1 | Rh2(S-DOSP)4 (1 mol %) | DIPEA | TFT | 25°C | 58% | 59% |
2 | Rh2(S-PTTL)4 (1 mol %) | DIPEA | TFT | 25°C | 66% | 87% |
3 | Rh2(S-PTAD)4 (1 mol %) | DIPEA | TFT | 25°C | 61% | 91% |
4 | Rh2(S-BTPCP)4 (1 mol %) | DIPEA | TFT | 25°C | N.D. | – |
5 | Rh2(S-PTAD)4 (1 mol %) | K2CO3 | TFT | 25°C | N.R. | – |
6 | Rh2(S-PTAD)4 (1 mol %) | CsCO3 | TFT | 25°C | N.R. | – |
7 | Rh2(S-PTAD)4 (1 mol %) | tBuOK | TFT | 25°C | N.R. | – |
8 | Rh2(S-PTAD)4 (1 mol %) | DIPEA | Toluene | 25°C | 53% | 82% |
9 | Rh2(S-PTAD)4 (1 mol %) | DIPEA | DCM | 25°C | 47% | 20% |
10 | Rh2(S-PTAD)4 (1 mol %) | DIPEA | DMF | 25°C | Trace | – |
11 | Rh2(S-PTAD)4 (1 mol %) | DIPEA | TFT | 40°C | 73% | 87% |
12 | Rh2(S-PTAD)4 (1 mol %) | DIPEA | TFT | 0°C | 21% | – |
13 | Rh2(S-PTAD)4 (0.5 mol %) | DIPEA | TFT | 25°C | 61% | 92% |
14 | Rh2(S-PTAD)4 (0.25 mol %) | DIPEA | TFT | 25°C | 50% | 74% |
15b | Rh2(S-PTAD)4 (0.5 mol %) | DIPEA | TFT | 25°C | 93% | 95% |
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N.D., Not detect.
Reaction conditions: N-Triftosylhydrazone 1 (0.2 mmol), 1,1-diphenylethylene 2 (0.1 mmol), [Rh] catalyst (1 mol %), DIPEA (N, N-diisopropylethylamine) (0.2 mmol), TFT (benzotrifluoride, 3.0 mL), 12 h, under N2.
α-Methyl-4-NO2-phenylethylene was used.