Table 13.
Enantioselective synthesis of chiral Troger’s bases employing a carbohydrate-derived chiral ionic liquid (CIL), as reported by Yuan et al. [83].
| Entry | R | X | t (h) | Yield (%) 1 | ee (%) 2 |
|---|---|---|---|---|---|
| 1 | CH3 | NPh | 5 | 83 | 98 |
| 2 | p-MePh | NPh | 7 | 76 | >99 |
| 3 | p-OMePh | NPh | 7 | 73 | >99 |
| 4 | CH 3 | p-MePhN | 6 | 71 | 90 |
| 5 | Ph | NPh | 7.5 | 70 | 84 |
| 6 | H | NPh | 9 | 79 | 44 3 |
| 7 | p-ClPh | NPh | 9 | 65 | Racemic |
| 8 | CH3 | O | 10 | 51 | Racemic |
1 Isolated yield; 2 Determined by HPLC (Chiralcel OD-H, IPA:Acetonitrile 15:85); 3Determined by HPLC (Chiralcel OD-H, IPA:Methanol 15:85).