Solvent screening for HDA reaction.
| |||||
|---|---|---|---|---|---|
| Entry | Solvent | Time (h) | Yielda (%) | drb | Eec (%) |
| 1 | Toluene | 48 | 86 | 80 20 | 92 |
| 2 | Benzene | 48 | 60 | 78 22 | 90 |
| 3 | Xylene | 48 | 73 | 77 23 | 88 |
| 4 | Cyclohexane | 48 | 66 | 74 26 | 89 |
| 5 | Hexane | 48 | trace | — | — |
| 6 | Et2O | 48 | 55 | 78 22 | 90 |
| 7 | iPr2O | 48 | 68 | 77 23 | 89 |
| 8 | THF | 48 | 40 | 79 21 | 82 |
| 9 | CH2Cl2 | 48 | 74 | 79 21 | 90 |
| 10 | CHCl3 | 48 | 34 | 84 16 | 92 |
| 11 | C2H4Cl2 | 48 | 75 | 77 23 | 88 |
| 12 | CH3CN | 48 | 70 | 75 25 | 88 |
| 13 | MeOH | 48 | 38 | 68 32 | 83 |
| 14 | Toluene | 24 | 73 | 79 21 | 90 |
| 15 | Toluene | 72 | 86 | 78 22 | 86 |
| 16 | Toluene | 96 | 78 | 78 22 | 86 |
| 17 | Neat | 24 | 87 | 71 29 | 86 |
| 18 | Neat | 48 | 75 | 68 32 | 82 |
Isolated yield.
Diastereoselectivity (dr) was determined by 1HNMR of the crude reaction mixture (major diastereomer: 8a).
The ee value were determined by HPLC (Daicel chiralpak IB column).