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

Model Michael addition in homogeneous environment catalyzed with Ida.

Entry Solvent Reaction time [h] Conversionb (isol. yieldc) [%] eed [%] syn : antib
1 Hexane 72 61 (32) 95 94 : 6
2 Toluene 48 Quant. (92) 89 91 : 9
3 DCM 72 77 (52) 80 90 : 10
4 MeOH 72 0
a

Reaction conditions: nitrostyrene 0.25 mmol, cyclohexanone 250 μl, Id 0.025 mmol, acetic acid 0.035 mmol, solvent 1 ml, t = 25 °C.

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).