Synthesis of Sulfonylated Cinchona Alkaloids via Zinc-Mediated Sulfonylation of the N-Oxides of the Quinoline Groups

Jie Zhou; Cheng-Yu Gu; Fu-She Han

doi:10.1055/a-1900-0293

Synthesis, Table of Contents

Synthesis 2022; 54(21): 4810-4817
DOI: 10.1055/a-1900-0293

paper

Synthesis of Sulfonylated Cinchona Alkaloids via Zinc-Mediated Sulfonylation of the N-Oxides of the Quinoline Groups

Jie Zhou

^aCAS Key Lab of High-Performance Synthetic Rubber and its Composite Materials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin 130022, P. R. of China

^bUniversity of Chinese Academy of Sciences, Beijing 100864, P. R. of China

,

Cheng-Yu Gu

^aCAS Key Lab of High-Performance Synthetic Rubber and its Composite Materials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin 130022, P. R. of China

^cUniversity of Science and Technology of China, Hefei, Anhui 230026, P. R. of China

,

Fu-She Han ∗

^aCAS Key Lab of High-Performance Synthetic Rubber and its Composite Materials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin 130022, P. R. of China

^cUniversity of Science and Technology of China, Hefei, Anhui 230026, P. R. of China

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Abstract

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Abstract

A general and practical method for the synthesis of sulfonylated cinchona alkaloids is presented. The reactions are carried out via Zn-mediated nucleophilic aromatic substitution of the N-oxides of the quinoline core in cinchona alkaloids with a range of sulfonyl chlorides. By careful optimization of the reaction parameters and the procedure, both aromatic and aliphatic sulfonyl chlorides react efficiently with the N-oxides to afford the corresponding sulfonylated products in high yields. In addition, the reaction can be reliably scaled up to gram level. As a result, this method provides a practical route for the synthesis of new cinchona alkaloid derivatives that might be potentially useful compounds, particularly in asymmetric catalysis.

Key words

cinchona alkaloids - quinoline N-oxides - quinolines - sulfonylation - nucleophilic aromatic substitution

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