Table 2.
Evaluation of the base sensitivity of Cyrene.a
| Entry | Base | Temp. (°C) | Reaction (Y/N)b |
| 1 | KOAc | 25 | N |
| 50 | Y | ||
| 100 | Y | ||
| 2 | Pyridine | 25 | N |
| 50 | Y | ||
| 100 | Y | ||
| 3 | K2CO3 | 25 | Y |
| 50 | Y | ||
| 100 | Y | ||
| 4 | DIPEA | 25 | N |
| 50 | N | ||
| 100 | Y | ||
| 5 | Cs2CO3 | 25 | Y |
| 50 | Y | ||
| 100 | Y | ||
| 6 | Et3N | 25 | N |
| 50 | N | ||
| 100 | Y | ||
| 7 | K3PO4 | 25 | Y |
| 50 | Y | ||
| 100 | Y | ||
| 8 | DBU | 25 | Y |
| 50 | Y | ||
| 100 | Y | ||
| 9 | KOH | 25 | Y |
| 50 | Y | ||
| 100 | Y | ||
| 10 | t-BuOK | 25 | Y |
| 50 | Y | ||
| 100 | Y | ||
| 11 | NaH | 25 | Y |
| 50 | Y | ||
| 100 | Y | ||
aReaction conditions: base (0.07 mmol) and Cyrene (0.5 mL) stirred at the indicated temeperature for 24 h before analysis by TLC and 1H NMR . bY = reaction occurs, N = no reaction. See Supporting Information File 1.