Qiao Jianhui, Liu Huili, Wang Shaozhong
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, National Center for Magnetic Resonance in Wuhan, Innovation Academy for Precision Measurement Science and Technology, Chinese Academy of Sciences, Wuhan 430071, China.
ACS Omega. 2021 Sep 14;6(38):25049-25061. doi: 10.1021/acsomega.1c04261. eCollection 2021 Sep 28.
A protocol has been developed to access indole-annulated eight- and nine-membered lactams through protonation-induced ring-opening of spiroindolines, which are dearomative Heck products of tetrahydro-β-carbolines or hexahydroazepino[3,4-]indoles. Brønsted acids and nucleophiles were explored and compared in the transformation. A combination of deuterated hydrochloride and deuterated methanol enables deuterative ring-opening of spiroindolines to afford medium-sized lactam diastereoisomers with a deuterium content ratio around 1:1.
已开发出一种方案，通过质子化诱导的螺吲哚啉开环来获得吲哚稠合的八元及九元内酰胺，螺吲哚啉是四氢-β-咔啉或六氢氮杂环庚并[3,4-]吲哚的去芳构化Heck产物。在该转化过程中对布朗斯特酸和亲核试剂进行了探索和比较。氘代盐酸盐和氘代甲醇的组合能够使螺吲哚啉发生氘代开环，从而得到氘含量比约为1:1的中等大小内酰胺非对映异构体。
