Model Michael addition: continuous flow reaction catalyzed with IIa and IId.
Entry | Catalyst | Solvent | Conversionc (isol. yieldd) [%] | eee [%] | syn : antic |
---|---|---|---|---|---|
1af | IIa | Neat | 32 (24) | 86 | 93 : 7 |
2bf | IId | Hexane | 7 (5) | 80 | 94 : 6 |
Reaction conditions: nitrostyrene 5.0 mmol, cyclohexanone 100 ml, acetic acid 50.0 mmol, flow 0.7 ml min−1, t = 25 °C, reaction time = 72 h.
Reaction conditions: nitrostyrene 5.0 mmol, cyclohexanone 100 ml, acetic acid 50.0 mmol, flow 0.7 ml min−1, 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).
Residence time = 42 min.