Asymmetric synthesis of fluoroalkylated N,O-ketals via an organocatalytic dehydration/aminalization/aza-Michael desymmetrization

Yang Gui; Xinping Liang; Yanan Li; Kuiliang Li; Zhenggen Zha; Zhiyong Wang

doi:10.1039/C8QO01397G

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Asymmetric synthesis of fluoroalkylated N,O-ketals via an organocatalytic dehydration/aminalization/aza-Michael desymmetrization†

Yang Gui,^a Xinping Liang,^a Yanan Li,^a Kuiliang Li,^a Zhenggen Zha^a and Zhiyong Wang

*^a

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* Corresponding authors

^a Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry & Collaborative Innovation Center of Suzhou Nano Science and Technology, Department of Chemistry, University of Science and Technology of China Hefei, Anhui 230026, China
E-mail: zwang3@ustc.edu.cn
Fax: (+86) 551-3603185

Abstract

A chiral C–O bond delivering chiral N,O-ketals was developed via an organocatalytic dehydration/aminalization/aza-Michael desymmetrization. A variety of fluoroalkylated N,O-ketals can be obtained with excellent yields (up to 98%) and good to excellent enantioselectivities (up to 92%).

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DOI: https://doi.org/10.1039/C8QO01397G
Article type: Research Article
Submitted: 24 Dec 2018
Accepted: 08 Feb 2019
First published: 12 Feb 2019

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Org. Chem. Front., 2019,6, 942-945

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Asymmetric synthesis of fluoroalkylated N,O-ketals via an organocatalytic dehydration/aminalization/aza-Michael desymmetrization

Y. Gui, X. Liang, Y. Li, K. Li, Z. Zha and Z. Wang, Org. Chem. Front., 2019, 6, 942 DOI: 10.1039/C8QO01397G

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Asymmetric synthesis of fluoroalkylated N,O-ketals via an organocatalytic dehydration/aminalization/aza-Michael desymmetrization†

Abstract

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Asymmetric synthesis of fluoroalkylated N,O-ketals via an organocatalytic dehydration/aminalization/aza-Michael desymmetrization

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