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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 16
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Articles

Asymmetric α-hydroxylation of β-dicarbonyl compounds by C-2′ modified cinchonine-derived phase-transfer catalysts in batch and flow microreactors

Xiao-Fei TangState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, P.R. China; ;Xi’an Modern Chemistry Research Institute, Xi’an, Shaanxi, P.R. ChinaView further author information
,
Jing-Nan ZhaoState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, P.R. China; View further author information
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Yu-Feng WuState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, P.R. China; View further author information
,
Ze-Hao ZhengState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, P.R. China; View further author information
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Cun-Fei MaState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, P.R. China; View further author information
,
Zong-Yi YuState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, P.R. China; View further author information
,
Lei YunState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, P.R. China; View further author information
,
Guang-Zhi LiuState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, P.R. China; View further author information
&
Qing-Wei MengState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, P.R. China; Correspondence[email protected]
View further author information
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Pages 2478-2487 | Received 30 Sep 2019, Published online: 24 Jun 2020
 
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Abstract

The asymmetric α-hydroxylation of β-dicarbonyl compounds was catalyzed by C-2′-modified cinchonine-derived phase-transfer catalysts. Excellent yields (up to 95%) and good enantioselectivities (up to 89% ee) were obtained. The reaction was carried out in a flow microreactor and similar results were obtained (up to 93% yield, 84% ee), the residence time was shortened from 24 h in batch to 2 h.

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Additional information

Funding

This work was supported by the National Natural Science Foundation of China (Nos. 21476041, U1608224, 61633006), and the State Key Laboratory of Fine Chemicals.

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