Organocatalyzed aldol reaction of acetone with p-nitrobenzaldehydea.
| |||||
|---|---|---|---|---|---|
| Entry | Cat | T | % convb | 10 : 11c | e. r.d |
| 1 | 4 | NO | 14 | 50 : 50 | 76 : 24 |
| 2 | 6a | NO | 58 | 91 : 9 | 76 : 24 |
| 3 | 6b | NO | 60 | 100 : 0 | 88 : 12 |
| 4 | 4 | YES | 76 | 83 17 | 62 : 38 |
| 6 | 6b | YES | 78 | 91 : 9 | 70 : 30 |
Reaction conditions: acetone (0.25 mmol), p-nitrobenzaldehyde (0.025 mmol), catalyst (10 mol%), N-hexylthymine (0 or 0.125 mmol), CH2Cl2 (100 μL), 25 °C, 4 days.
Determined by 1H NMR from the crude reaction.
Ratio of 10 : 11 was determined by 1H NMR analysis.
e. r. determined by HPLC using a Daicel ChiralPak AS-H column.