Scope of the Passerini reaction carried out in U/CC DES with chiral heterogeneous catalyst 11.
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|---|---|---|---|---|---|---|---|
| Entry | R1 in RCOOH 12 | R2 in RCHO 13 | R3 in RNC 14 | Time (h) | 15 | Yielda (%) | Eeb (%) |
| 1 | Ph; 12a | Ph; 13a | t-Bu; 14a | 20 | 15a | 87c | 94.8 |
| 2 | Ph; 12a | 3-NO2C6H4; 13b | t-Bu; 14a | 24 | 15b | 93 | 96.4 |
| 3 | Ph; 12a | 4-MeOC6H4; 13c | t-Bu; 14a | 20 | 15c | 85 | 96.8 |
| 4 | Ph; 12a | 4-ClC6H4; 13d | t-Bu; 14a | 22 | 15d | 93 | 96.9 |
| 5 | Ph; 12a | 4-MeC6H4; 13e | t-Bu; 14a | 24 | 15e | 87 | 97.6 |
| 6 | Ph; 12a | PhCH CH; 13f | t-Bu; 14a | 28 | 15f | 86 | 92.7 |
| 7 | Ph; 12a | i-Pr; 13g | t-Bu; 14a | 20 | 15g | 87 | 95.5 |
| 8 | 4-NO2C6H4; 12b | Ph; 13a | t-Bu; 14a | 24 | 15h | 84 | 95.6 |
| 9 | 4-MeOC6H4; 12c | Ph; 13a | t-Bu; 14a | 30 | 15i | 87 | 95.9 |
| 10 | 4-ClC6H4; 12d | Ph; 13a | t-Bu; 14a | 20 | 15j | 90 | 96.8 |
| 11 | Me; 12e | Ph; 13a | t-Bu; 14a | 20 | 15k | 86 | 96.5 |
| 12 | PhCH2; 12f | Ph; 13a | t-Bu; 14a | 22 | 15l | 87 | 93.1 |
| 13 | 3-Pyridyl; 12g | 4-ClC6H4; 13d | t-Bu; 14a | 24 | 15m | 78 | 96.5 |
| 14 | Ph; 12a | Ph; 13a | 2-Naphthyl; 14b | 20 | 15n | 87 | 98.4 |
| 15 | Ph; 12a | 4-ClC6H4; 13d | 2-Naphthyl; 14b | 20 | 15o | 83 | 95.3 |
| 16 | Me; 12e | 3-NO2C6H4; 13b | 2-Naphthyl; 14b | 24 | 15p | 84 | 97.6 |
| 17 | Me; 12e | i-Pr; 13g | 2-Naphthyl; 14b | 22 | 15q | 86 | 96.1 |
Yields refer to pure and isolated 15. Times and yields refer to the reactions carried out with 1 mmol of 12a, 13a, 14a with chiral catalyst 11 (5% mol).
Enantiomeric excess was determined by chiral analyses on HPLC (ee).
The same results were obtained using 10 mol% of catalyst 11.