Nickel(II)-catalyzed enantioselective α-alkylation of β-ketoamides with phenyliodonium ylide via a radical process

Jing Guo; Xiaohua Liu; Changqiang He; Fei Tan; Shunxi Dong; Xiaoming Feng

doi:10.1039/C8CC07140C

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Nickel(ii)-catalyzed enantioselective α-alkylation of β-ketoamides with phenyliodonium ylide via a radical process†

Jing Guo,

^a Xiaohua Liu,

*^a Changqiang He,

^a Fei Tan,

^a Shunxi Dong

^a and Xiaoming Feng

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
E-mail: liuxh@scu.edu.cn, xmfeng@scu.edu.cn
Fax: +86 28 85418249

Abstract

Chiral Lewis acid-promoted enantioselective α-alkylation of β-ketoamides with phenyliodonium ylide was developed. In the presence of a chiral N,N′-dioxide/Ni(II) complex, the corresponding 1,4-dicarbonyl compounds were obtained with good results (up to 91% yield and 97% ee). Control experiments and EPR studies supported a radical process.

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Article information

DOI: https://doi.org/10.1039/C8CC07140C
Article type: Communication
Submitted: 03 Sep 2018
Accepted: 05 Oct 2018
First published: 05 Oct 2018

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Chem. Commun., 2018,54, 12254-12257

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Nickel(II)-catalyzed enantioselective α-alkylation of β-ketoamides with phenyliodonium ylide via a radical process

J. Guo, X. Liu, C. He, F. Tan, S. Dong and X. Feng, Chem. Commun., 2018, 54, 12254 DOI: 10.1039/C8CC07140C

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Chemical Communications

Nickel(ii)-catalyzed enantioselective α-alkylation of β-ketoamides with phenyliodonium ylide via a radical process†

Abstract

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Nickel(II)-catalyzed enantioselective α-alkylation of β-ketoamides with phenyliodonium ylide via a radical process

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