Recent progress in asymmetric rearrangement reactions mediated by chiral Brønsted acids

被引:2
|
作者
Liu, Xi-Liang [1 ]
Gong, Mei-Ling [1 ]
Yang, Xiaodi [1 ]
Tian, Ping [1 ]
Li, Qing-Hua [1 ]
机构
[1] Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, Res Ctr Chiral Drugs, Shanghai 201203, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 17期
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
CLAISEN REARRANGEMENT; PINACOL REARRANGEMENT; NATURAL-PRODUCTS; SEMIPINACOL REARRANGEMENT; PHOSPHORIC-ACIDS; CATALYSIS; MIGRATION;
D O I
10.1039/d4qo00807c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rearrangement reactions, a fundamental tool for constructing complex molecules, offer an atom-economical approach to target molecule synthesis. Chiral acid-mediated rearrangement reactions provide a powerful tool for the synthesis of enantioenriched molecules, crucial for synthesizing natural products, developing new drugs, and constructing functional materials. Herein we have categorized the 15 chiral Br & oslash;nsted acid mediated rearrangements based on the rearrangement mode, such as C-C bond cleavage/formation, skeletal rearrangements, and migration reactions. This review can delve deeper into specific examples within each rearrangement type, highlighting the reaction mechanisms, catalyst design strategies, and substrate scope. Additionally, this review provides a systematic analysis of chiral Br & oslash;nsted acid catalysis in rearrangement reactions, highlighting its unique value and contribution to the field of asymmetric synthesis. We believe that this review can offer valuable insights into the application of chiral Br & oslash;nsted acid catalysis in rearrangement reactions, a topic of significant interest to both medical and synthetic organic chemists. This review presents an overview of recent developments and trends in chiral Br & oslash;nsted acid mediated rearrangement reactions. Different mechanisms and activation modes are summarized to illustrate the regio- and stereo-selectivity in the reactions.
引用
收藏
页码:4934 / 4953
页数:20
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