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

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
a

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.

b

Determined by 1H NMR.

c

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

d

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