College of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, Wuhan, Hubei 430072, People's Republic of China.
School of Chemical Engineering & Pharmacy, School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan, Hubei 430205, People's Republic of China.
Org Lett. 2023 Feb 24;25(7):1172-1177. doi: 10.1021/acs.orglett.3c00148. Epub 2023 Feb 13.
Chiral benzoxazinones and 4-3,1-benzoxazines as important motifs are widely found in abundant pharmaceuticals and biological molecules. We herein successfully developed the first kinetic resolution (KR) process of racemic benzoxazinones through Ir-catalyzed asymmetric intramolecular allylation, furnishing a wide range of chiral benzoxazinones and 4-3,1-benzoxazines with excellent results via outstanding KR performances (with the factor up to 170). This protocol exhibited broad substrate scope generality and good functional group tolerance, and the chiral 4-3,1-benzoxazine products could be readily transformed to other useful optically active heterocycles.
手性苯并恶嗪酮和 4-3,1-苯并恶嗪作为重要的结构单元广泛存在于丰富的药物和生物分子中。本文通过铱催化的不对称分子内烯丙基化反应，成功开发了外消旋苯并恶嗪酮的首例动力学拆分（KR）过程，通过优异的 KR 性能（最高因子达到 170），以优异的结果得到了广泛的手性苯并恶嗪酮和 4-3,1-苯并恶嗪。该方案表现出广泛的底物范围通用性和良好的官能团耐受性，并且手性 4-3,1-苯并恶嗪产物可以很容易地转化为其他有用的光学活性杂环。
