Model Michael addition in heterogeneous environment catalyzed with IIa–da.
| Entry | Catalyst | Reaction time [h] | Conversionb (isol. yieldc) [%] | eed [%] | syn : antib |
|---|---|---|---|---|---|
| 1 | IIa | 72 | 51 (36) | 78 | 95 : 5 |
| 2 | IIb | 72 | 49 (18) | 90 | 90 : 10 |
| 3 | IIc | 72 | 10 (7) | 58 | 83 : 17 |
| 4 | IId | 72 | 25 (10) | 86 | 94 : 6 |
Reaction conditions: nitrostyrene 0.25 mmol, cyclohexanone 1 ml, catalyst 0.05 mmol, acetic acid 0.035 mmol, 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).