Citation: Yao Yuanyong, Shu Hua, Xing Mingming, Chen Shixue, Lu Zhongying, Tang Bangcheng. Utilization of Solid Acid SO₄^2-/TiO₂ Cooperated with CinchonaAlkaloid Quinidine to Asymmetric Mannich Organocatalysis[J]. Chinese Journal of Organic Chemistry, ;2015, 36(1): 196-201. doi: 10.6023/cjoc201507036 shu

Utilization of Solid Acid SO₄^2-/TiO₂ Cooperated with CinchonaAlkaloid Quinidine to Asymmetric Mannich Organocatalysis

1.
Institute of Applied Chemistry, School of Material and Chemical Engineering, Tongren University, Tongren 554300

Corresponding author: Shu Hua, yyy0326.love@163.com Tang Bangcheng,
Received Date: 28 July 2015
Revised Date: 10 September 2015

Fund Project: Foundation of Guizhou Educational Ministry Science and Technology KY(2012)069Youth Foundation of Guizhou Educational Ministry Science and Technology KY (2014)317

Figures(2)

Via combination of solid acid SO₄^2-/TiO₂ with cinchona alkaloid quinidine (R), the chiral catalyst of SO₄^2-/TiO₂/quinidine (R) carrying strong hydrogen-bonding donor has been obtained, which was evaluated on catalytic activity in the asymmetric organocatalysis, as comparing with quinidine (R) and thiourea-quinidine (R) derived from cinchona alkaloids. The result obviously showed that under the same conditions, the catalytic activity of SO₄^2-/TiO₂/quinidine (R) is more than that of quinidine (R), but less than that of thiourea-quinidine (R). Simultaneously, chiral β-amino ester derivatives with high optical activities were afforded under the optimum conditions of m-xylene as solvent and stirring for 72 h at －40 ℃. The value of ee was allowed to be the range of 89%～95%.
- β-amino esters,
- asymmetric Mannich organocatalysis,
- solid acid SO₄^2-/TiO₂,
- cinchona alkaloid quinidine
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Utilization of Solid Acid SO42-/TiO2 Cooperated with CinchonaAlkaloid Quinidine to Asymmetric Mannich Organocatalysis

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通讯作者: 陈斌, bchen63@163.com

Utilization of Solid Acid SO₄^2-/TiO₂ Cooperated with CinchonaAlkaloid Quinidine to Asymmetric Mannich Organocatalysis