Download PDF
Synthesis 2023; 55(23): 3991-3999
DOI: 10.1055/a-2135-9037
paper

A Concise and Flexible Synthesis of C2′-Sulfonylated Quinine Derivatives

Cheng-Yu Gu
a   CAS 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
b   School of Applied Chemistry and Engineering, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China
,
Jie Zhou
a   CAS 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
b   School of Applied Chemistry and Engineering, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China
,
Dong-Xing Tan∗
a   CAS 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
,
Fu-She Han  ∗
a   CAS 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
b   School of Applied Chemistry and Engineering, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China
› Author AffiliationsFinancial support from the National Natural Science Foundation of China (22071235) is acknowledged.
› Further Information
    Permissions and Reprints All articles of this category


Abstract

A concise and flexible procedure for the synthesis of structurally novel C2′-sulfonylated quinine derivatives is developed. Through careful optimization of the reaction conditions, most of the reactions can be performed in high yields at gram or several hundreds of milligram scale. Since cinchona-based derivatives are widely used in asymmetric catalysis, the synthetic route developed herein provides an efficient and practical pathway for the diverse synthesis of new cinchona derivatives as potential chiral ligands or multifunctional organocatalysts.

Key words

cinchona alkaloid derivatives - synthesis - sulfonylation - asymmetric catalysis - organocatalyst

Supporting Information

    Supporting information for this article is available online at https://doi.org/ 10.1055/a-2135-9037.
  • Supporting Information


Publication History

Received: 26 June 2023

Accepted after revision: 24 July 2023

Accepted Manuscript online:
24 July 2023

Article published online:
07 September 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany