A facile approach to C-functionalized β-ketoimine compounds via terminal alkylation of a tetralithiated intermediate

Shuai Zhou; Xiaojuan Xu; Xu Zhu; Yu Zheng; Sufang Chen; Mingqiang Xue

doi:10.1039/D2OB00640E

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A facile approach to C-functionalized β-ketoimine compounds via terminal alkylation of a tetralithiated intermediate†

Shuai Zhou,^a Xiaojuan Xu,^a Xu Zhu,^a Yu Zheng,

^b Sufang Chen^a and Mingqiang Xue

*^a

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* Corresponding authors

^a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
E-mail: xuemingqiang@suda.edu.cn

^b College of Chemical Engineering, Nanjing Forestry University, Nanjing, China

Abstract

A series of C-functionalized β-ketoimine compounds at the terminal methyl groups of the β-ketoimine precursor L^phH₂ (L^ph = C₆H₄[NC(Me) [double bond, length as m-dash] CHC(Me)O]₂) were prepared. This convenient transformation was realized via straightforward double alkylation on the terminal C_α of a novel bis-dianionic β-ketoiminate lithium complex [L^ph′Li₄(THF)₄]₂ (L^ph′ = C₆H₄[NC(Me)CHC(O)CH₂]₂) followed by hydrolysis.

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DOI: https://doi.org/10.1039/D2OB00640E
Article type: Communication
Submitted: 05 Apr 2022
Accepted: 06 May 2022
First published: 06 May 2022

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Org. Biomol. Chem., 2022,20, 4289-4292

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A facile approach to C-functionalized β-ketoimine compounds via terminal alkylation of a tetralithiated intermediate

S. Zhou, X. Xu, X. Zhu, Y. Zheng, S. Chen and M. Xue, Org. Biomol. Chem., 2022, 20, 4289 DOI: 10.1039/D2OB00640E

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Organic & Biomolecular Chemistry

A facile approach to C-functionalized β-ketoimine compounds via terminal alkylation of a tetralithiated intermediate†

Abstract

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A facile approach to C-functionalized β-ketoimine compounds via terminal alkylation of a tetralithiated intermediate

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