% Yield and % ee of (S)-2-[(R)-hydroxy(4-nitrophenyl)methyl] cyclohexan-1-one and (S)-2-[(R)-hydroxy(4-methoxyphenyl)methyl] cyclohexan-1-one.
| Entry | Catalysts | (S)-2-[(R)-hydroxy(4-nitrophenyl)methyl] cyclohexan-1-one | (S)-2-[(R)-hydroxy(4-methoxyphenyl)methyl] cyclohexan-1-one | ||
|---|---|---|---|---|---|
| % Yield | % ee | % Yield | % ee | ||
| 1 | No catalysta | 67.2 | 0 | 1.1 | 0 |
| 2 | Prolineb | 41.8 | 73.2 | 83.0 | 99.4 |
| 3 | P1 | 53.8 | 22.2 | 21.5 | 0 |
| 4 | CuP1 | 18.1 | 87.2 | 84.7 | 95.5 |
| 5 | P2 | 66.5 | 22.9 | 25.8 | 0 |
| 6 | CuP2 | 31.5 | 88.7 | 3.3 | 68.2 |
| 7 | P3 | 41.9 | 94.4 | 84.4 | 97.5 |
| 8 | CuP3 | 40.2 | 80.2 | 29.6 | 91.0 |
| 9 | P4c | 55.0 | 98.0 | 91.2 | 98.4 |
| 10 | CuP4 | 50.5 | 0 | 22.1 | 0 |
| 11 | P5 | 56.6 | — | 39.6 | 99.0 |
| 12 | CuP5 | 50.7 | 0 | 21.2 | 94.4 |
Negative control.
Positive control.
P4 was observed to be the best catalyst for both the aldol reactions, followed by P3. The copper-peptides (exceptional for CuP4) catalyzed both the aldol reactions with higher enantioselectivity (94–98%) and yield of products as compared to proline.