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. 2018 Jan 3;8(3):1174–1181. doi: 10.1039/c7ra12658a

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
a

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.

b

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.

c

Determined by 1H NMR.

d

Purified by column chromatography (hexane : ethyl acetate = 5 : 1).

e

Determined by chiral HPLC (column YMC Amylose C, mobile phase heptane : IPA = 9 : 1, flow rate 0.7 ml min−1).

f

Residence time = 42 min.