Copper-catalyzed enantioselective Mukaiyama aldol reaction of silyl enol ethers with isatins

Jindong Li; Yanan Li; Jianan Sun; Yang Gui; Yekai Huang; Zhenggen Zha; Zhiyong Wang

doi:10.1039/C9CC02159K

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Copper-catalyzed enantioselective Mukaiyama aldol reaction of silyl enol ethers with isatins†

Jindong Li,^a Yanan Li,^a Jianan Sun,^a Yang Gui,^a Yekai Huang,^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 & Center for Excellence in Molecular Synthesis of Chinese Academy of Sciences, Collaborative Innovation Center of Suzhou Nano Science and Technology & School of Chemistry and Materials Science in University of Science and Technology of China, Hefei, P. R. China
E-mail: zwang3@ustc.edu.cn

Abstract

A highly enantioselective Mukaiyama aldol reaction of silyl enol ethers with isatins catalyzed by chiral copper complexes was developed. A series of chiral 3-substituted 3-hydroxy-2-oxindoles bearing a tetra-substituted center could be obtained exclusively with high yields (up to 95%) and excellent enantioselectivities (up to 99%). In particular, water was essential to improve the diastereoselectivity.

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DOI: https://doi.org/10.1039/C9CC02159K
Article type: Communication
Submitted: 18 Mar 2019
Accepted: 07 May 2019
First published: 07 May 2019

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Chem. Commun., 2019,55, 6309-6312

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Copper-catalyzed enantioselective Mukaiyama aldol reaction of silyl enol ethers with isatins

J. Li, Y. Li, J. Sun, Y. Gui, Y. Huang, Z. Zha and Z. Wang, Chem. Commun., 2019, 55, 6309 DOI: 10.1039/C9CC02159K

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Chemical Communications

Copper-catalyzed enantioselective Mukaiyama aldol reaction of silyl enol ethers with isatins†

Abstract

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Copper-catalyzed enantioselective Mukaiyama aldol reaction of silyl enol ethers with isatins

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