Screening additive and temperaturea.
| Entry | Additive | T (°C) | Yieldb (%) | drc (anti/syn) | eec (%) |
|---|---|---|---|---|---|
| 1 | 4-NO2PhCOOH | rt | 98 | 97 : 3 | 94 |
| 2 | PhCOOH | rt | 98 | 96 : 4 | 95 |
| 3 | CF3OOH | rt | 96 | 96 : 4 | 93 |
| 4 | CH3OOH | rt | 95 | 95 : 5 | 94 |
| 5 | HCOOH | rt | 96 | 95 : 5 | 93 |
| 6 | — | rt | 95 | 98 : 2 | 95 |
| 7 | — | 10 | 95 | 98 : 2 | 95 |
| 8 | — | 0 | 93 | 98 : 2 | 96 |
| 9d | — | 0 | 98 | 98 : 2 | 96 |
Reaction conditions: p-nitrobenzaldehyde (0.5 mmol), cyclohexanone (10 equiv.), catalyst 1d (0.05 mmol, 10 mol%), solvent (1.0 mL), room temperature, 36 hours with vigorous stirring.
Combined yields of isolated.
Determined by HPLC with a chiral AD-H column.
Vigorous stirring for 48 hours.