Model Michael addition in heterogeneous environment catalyzed with IIa and IIda.
| Entry | Catalyst | Solvent | Conversionb (isol. yieldc) [%] | eed [%] | syn : antib |
|---|---|---|---|---|---|
| 1 | IIa | neate | 51 (36) | 78 | 95 : 5 |
| 2 | IIa | Neate | 34 (17) | 72 | 94 : 6 |
| 3 | IIa | Neate | 37 (20) | 70 | 96 : 4 |
| 4 | IIa | Neate | 32 (18) | 69 | 96 : 4 |
| 5 | IIa | Neate | 35 (21) | 69 | 93 : 7 |
| 6 | IId | Hexane | 37 (21) | 80 | 94 : 6 |
| 7 | IId | Hexane | 21 (13) | 80 | 95 : 5 |
| 8 | IId | Hexane | 20 (11) | 89 | 92 : 8 |
| 9 | IId | Hexane | 22 (13) | 81 | 94 : 6 |
| 10 | IId | Hexane | 19 (12) | 79 | 93 : 7 |
Reaction conditions: nitrostyrene 0.25 mmol, cyclohexanone 250 μl, catalyst 0.05 mmol, acetic acid 0.035 mmol, solvent 1 ml, t = 25 °C, reaction time = 72 h.
Determined by 1H NMR.
Purified by column chromatography (hexane : ethyl acetate = 5 : 1).
Determined by chiral HPLC (column YMC Amylose C, mobile phase heptane : IPA = 9 : 1, flow rate 0.7 ml min−1).
Additional 750 μl of cyclohexanone was used instead of the solvent.