Thermodynamic Resolution of Pharmaceutical Precursor Modafinil Acid on the Basis of Chiral-at-Metal Strategy

• 作者: Man-Li Cao Jun-Ling Zhu Zhong-Lan Zhi Bao-Hui Ye Su-Yang Yao Xiu-Lian Zhang
• 来源期刊: 中国化学（英文版）
• 年，卷（期）: 2021,（6）
• 所属期刊栏目: Concise Reports
• 页码范围: 1483-1490
• 页数: 8页
• 语种: 英文
• DOI: 10.1002/cjoc.202000729

摘要

Main observation and conclusion Chiral-at-metal strategy was developed to resolve the essential sulfoxide pharmaceutical intermediates R-modafinil acid and its ana-logues with high yields and ee values.The efficient resolution process was achieved based on the diastereoselective discrimination caused by hydrogen bond and intramolecular π-n interaction between chiral-at-metal center and the coordinated chiral sulfoxide ligands.Moreover,the chiral Ir(Ⅲ)receptor can be reused with complete retention of their configurations and without the loss of re-action activity and enantioselectivity.This work provides a new access to synthesize R-modafinil acid as well as its analogues and de-velops the application of chiral-at-metal strategy in chiral resolution.