Model Michael addition in homogeneous environment catalyzed with Ida.
Entry | Solvent | Reaction time [h] | Conversionb (isol. yieldc) [%] | eed [%] | syn : antib |
---|---|---|---|---|---|
1 | Hexane | 72 | 61 (32) | 95 | 94 : 6 |
2 | Toluene | 48 | Quant. (92) | 89 | 91 : 9 |
3 | DCM | 72 | 77 (52) | 80 | 90 : 10 |
4 | MeOH | 72 | 0 | — | — |
Reaction conditions: nitrostyrene 0.25 mmol, cyclohexanone 250 μl, Id 0.025 mmol, acetic acid 0.035 mmol, solvent 1 ml, t = 25 °C.
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).