Influence of the catalyst structure.
| |||||||
|---|---|---|---|---|---|---|---|
| Entry | Cat. | X (mol%) | Solvent | Time (d) | Yielda (%) | syn : antib | eec (%) |
| 1d | DABCO | 20 | DCM | 2 | 45 | 1 : 1.2 | — |
| 2 | 3a | 20 | Toluene | 4 | 80 | 5.4 : 1 | 88 |
| 3e | 3a | 20 | Toluene | 7 | 76 | 7.0 : 1 | 93 |
| 4 | 4a | 20 | Toluene | 4 | 80 | 1 : 11 | 56 |
| 5f | 4a | 5 | DCE | 2 | 95 | 1 : 24 | 70 |
| 6f | 4b | 5 | DCE | 2 | 90 | 1 : 15 | 95 |
| 7 | 8 | 20 | Toluene | 4 | 52 | 3.9 : 1 | 72 |
| 8 | 9 | 20 | Toluene | 4 | 51 | 3.5 : 1 | 73 |
| 9 | 6a | 20 | Toluene | 4 | 33 | 1.6 : 1 | 56 |
| 10 | 10 | 20 | Toluene | 4 | 79 | 1 : 5.2 | 63 |
| 11 | 11 | 20 | Toluene | 1 | 89 | 1 : 3.0 | 61 |
| 12 | 12 | 20 | Toluene | 1 | 63 | 1.2 : 1 | 84 |
Isolated yield.
Determined by 1H NMR analysis of the crude mixture.
Determined by HPLC analysis.
Room temperature.
0.3 mmol, with 90 mg powdered 5 Å MS, [1a] = 0.3 M.
[1a] = 0.1 M. [1a] = 0.2 M without noted. DCM: CH2Cl2. DCE : CH2ClCH2Cl.