Table 7.
Time dependent domino aldol reactions of different aldehydes and ketones having H, F and MeO units at para-position of phenyl units using ZrCl4. Yields are in % and numbers in brackets are for mono aldol products (reaction time: 2 h, reaction temperature: 25 °C).
 |
 |
 |
||||||||
| 1a | 1b | 1c | ||||||||
 3a–c |
H (3a) | F (3c) | MeO (3d) | H (3a) | F (3c) | MeO (3d) | H (3a) | F (3c) | MeO (3d) | |
| Entry | Time [min] | 5a | 5c | 5d | 7a | 9a | 9b | 7b | 9c | 9d |
| 1 | 5 | 5 (+10) |
9 (+9) |
7 (+12) |
5 (+15) |
5 (+18) |
8 (+14) |
25 (+7) |
26 (+11) |
15 (+19) |
| 2 | 10 | 8 (+16) |
23 (+10) |
10 (+15) |
6 (+20) |
8 (+19) |
10 (+15) |
28 (+8) |
26 (+11) |
17 (+15) |
| 3 | 20 | 19 (+16) |
27 (+8) |
15 (+17) |
8 (+16) |
12 (+15) |
14 (+17) |
29 (+7) |
28 (+20) |
20 (+9) |
| 4 | 30 | 27 (+18) |
35 (+10) |
16 (+16) |
12 (+16) |
15 (+19) |
20 (+16) |
32 (+12) |
32 (+12) |
25 (+11) |
| 5 | 45 | 44 (+19) |
51 (+9) |
20 (+13) |
19 (+19) |
20 (+17) |
30 (+17) |
37 (+6) |
36 (+17) |
29 (+10) |
| 6 | 60 | 60 (+20) |
52 (+10) |
35 (+12) |
24 (+18) |
21 (+18) |
37 (+15) |
40 (+6) |
44 (+11) |
30 (+9) |
| 7 | 120 | 76 (+8) |
62 (+7) |
45 (+5) |
40 (+20) |
29 (+17) |
54 (+14) |
45 (+4) |
58 (+14) |
32 (+14) |