Model Michael addition in heterogeneous environment catalyzed with IIa and IIda.
Entry | Catalyst | Solvent | Conversionb (isol. yieldc) [%] | eed [%] | syn : antib |
---|---|---|---|---|---|
1 | IIa | Hexane | 44 (23) | 82 | 92 : 8 |
2 | IIa | Toluene | 51 (38) | 78 | 94 : 6 |
3 | IIa | DCM | 39 (16) | 70 | 92 : 8 |
4 | IIa | MeOH | 16 (10) | 46 | 82 : 18 |
5 | IId | Hexane | 37 (21) | 80 | 94 : 6 |
6 | IId | Toluene | 23 (15) | 78 | 94 : 6 |
7 | IId | DCM | 17 (10) | 74 | 92 : 8 |
8 | IId | MeOH | 7 (3) | 53 | 86 : 14 |
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).