Skip to main content
. 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 neate 51 (36) 78 95 : 5
2 IIa Neate 34 (17) 72 94 : 6
3 IIa Neate 37 (20) 70 96 : 4
4 IIa Neate 32 (18) 69 96 : 4
5 IIa Neate 35 (21) 69 93 : 7
6 IId Hexane 37 (21) 80 94 : 6
7 IId Hexane 21 (13) 80 95 : 5
8 IId Hexane 20 (11) 89 92 : 8
9 IId Hexane 22 (13) 81 94 : 6
10 IId Hexane 19 (12) 79 93 : 7
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).

e

Additional 750 μl of cyclohexanone was used instead of the solvent.