Table 1.
Optimization of the Reaction Conditions
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|---|---|---|---|---|---|
| entry | catalyst | solvent (M) | time [h] | yield (%) | ee (%) |
| 1 | - | PhMe (2) | 24 | 50 | - |
| 2 | 1a | PhMe (2) | 23 | 86 | 0 |
| 3 | 1b | PhMe (2) | 22 | 94 | 0 |
| 4 | 1c | PhMe (2) | 20 | 87 | 11 |
| 5 | 1d | PhMe (2) | 20 | 90 | −28 |
| 6 | 1e | PhMe (2) | 4 | 93 | 43 |
| 7 | 1f | PhMe (2) | 7 | 91 | 34 |
| 8 | 1g | PhMe (2) | 5 | 93 | 46 |
| 9 | 1h | PhMe (2) | 4 | 93 | 58 |
| 10 | 1i | PhMe (2) | 4 | 92 | 55 |
| 11 | 1j | PhMe (2) | 5 | 95 | 50 |
| 12 | 1k | PhMe (2) | 4 | 94 | 58 |
| 13 | 1l | PhMe (2) | 4 | 92 | 59 |
| 14 | 1m | PhMe (2) | 18 | 92 | 53 |
| 15 | 1n | PhMe (2) | 3 | 93 | 71 |
| 16a | 1o | PhMe (2) | 3 | 93 | 76 |
| 17 | 1o | PhMe (0.5) | 16 | 91 | 84 |
| 18 | 1o | PhMe (0.2) | 20 | 89 | 86 |
| 19 | - | PhMe (0.2) | 24 | trace | - |
| 20 | 1o | TBME (0.2) | 24 | 86 | 85 |
| 21 | 1o | CHCl3 (0.2) | 24 | 92 | 75 |
| 22a | 1o | PhCF3 (0.2) | 24 | 92 | 79 |
| 23 | 1o | PhH (0.2) | 24 | 92 | 84 |
| 24 | 1p | PhMe (0.2) | 22 | 92 | 85 |
| 25 | 1q | PhMe (0.2) | 24 | 92 | 88 |
| 26b | 1q | PhMe (0.2) | 34 | 89 | 88 |
| 27b,c | 1q | PhMe (0.2) | 72 | 90 | 93 |
Reaction mixture was partially heterogeneous.
Reaction was performed with 10 mol % catalyst.
Reaction was performed at −10 °C.
