From L-menthol, 5-(2-hydroxyethyl)-4-methylthiazole, paraformaldehyde and epoxyethane, a novel thermoregulated thiazolium chiral ionic liquid was synthesized and used for catalyzing the reaction of trans-cinnamaldehyde with methyl p-formylbenzoate to stereoselectively synthesize γ-butyrolactones with two chiral centres. By using the thermoregulation of the catalyst, the catalytic reaction in the thermoregulated solvent had the feature of "Thermoregulated Phase-separable Catalysis", and the recycling of the ionic liquid catalyst was easily achieved. THF/n-hexane (V:V=2.5:2) mixed solvent was selected as the thermoregulated solvent. Under the conditions of 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) as the alkaline reagent, the quantity of catalyst 10 mol%, the reaction temperature 35 ℃, and the reaction time 16 h, the conversion of trans-cinnamaldehyde could reach 95.4%, and the selectivity of γ-butyrolactones was 80.4%. The ratio of cis/trans product was 3.3, and the ee values of cis-product and trans-product were 21.3% and 16.1%, respectively. The recycling efficiency of the ionic liquid catalyst was investigated. During the recycles of 4 times, the catalytic activity of the ionic liquid was nearly unchanged.
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