Table 2.
Entry | R | er | Charton value | △△G≠ (kcal K−1 mol−1)b |
---|---|---|---|---|
1 | OMe | 88.06:11.94 | 0.36 | 1.16 |
2 | OEt | 96.0:4.0 | 0.48 | 1.85 |
3 | Ph | 96.52:3.48 | 0.57 | 1.93 |
4 | Me | 92.42:7.58 | 0.52 | 1.46 |
5 | Et | 94.02:5.98 | 0.56 | 1.60 |
6 | nBu | 95.45:4.55 | 0.68 | 1.77 |
7 | iPr | 96.66:3.34 | 0.76 | 1.96 |
8 | Cl | 18.32:81.68 | 0.55 | 0.87 |
9 | Br | 16.95:83.05 | 0.65 | 0.93 |
aReaction conditions: 1 (0.1 mmol), CuCl (10 mol%), L1 (15 mol%), (R)-CPA (0.1 mmol), toluene (2.0 mL), 20 °C for 36 h. Yields of isolated products, er values were determined by chiral HPLC.
bΔΔG≠ = RTln(er), R = 0.001986 kcal K−1 mol−1, T = 293.15 K.