Optimization of the reaction conditionsa.
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Entry | Catalyst | Solvent | Yieldb (%) | eec (%) |
1 | (S)-4.1a | DCE | 60 | 42 |
2 | (S)-4.1b | DCE | 73 | 38 |
3 | (S)-4.1c | DCE | 80 | 66 |
4 | (S)-4.1d | DCE | 64 | 2 |
5 | (S)-4.1e | DCE | 81 | 30 |
6 | (S)-4.1f | DCE | 47 | 18 |
7 | (S)-4.1g | DCE | 89 | 63 |
8 | (S)-4.1h | DCE | 71 | 58 |
9 | (S)-4.1i | DCE | 86 | 72 |
10 | (R)-4.2a | DCE | 72 | 32 |
11 | (R)-4.3a | DCE | 75 | 34 |
12 | (S)-4.1i | DCM | 79 | 64 |
13 | (S)-4.1i | CHCl3 | 83 | 64 |
14 | (S)-4.1i | Et2O | 59 | 52 |
15 | (S)-4.1i | EA | 74 | 59 |
16 | (S)-4.1i | 1,4-Dioxane | 80 | 32 |
17d | (S)-4.1i | DCE | 86 | 86 |
18 e | (S)-4.1i | DCE | 88 | 87 |
19f | (S)-4.1i | DCE | 56 | 79 |
Reaction conditions: 1a (0.05 mmol), 2a (0.06 mmol) and catalyst (10 mol%) in DCE (0.5 mL) at room temperature for 12 h.
Isolated yields.
Determined by chiral HPLC analysis.
3 Å MS.
4 Å MS.
At 0 °C.