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

Model Michael addition in heterogeneous environment catalyzed with IIa–da.

Entry Catalyst Reaction time [h] Conversionb (isol. yieldc) [%] eed [%] syn : antib
1 IIa 72 51 (36) 78 95 : 5
2 IIb 72 49 (18) 90 90 : 10
3 IIc 72 10 (7) 58 83 : 17
4 IId 72 25 (10) 86 94 : 6
a

Reaction conditions: nitrostyrene 0.25 mmol, cyclohexanone 1 ml, catalyst 0.05 mmol, acetic acid 0.035 mmol, 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).