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Diastereoselective Intramolecular Spirocyclization via C(sp3)‐H Bond Functionalization Towards the Synthesis of 2,7‐Diazaspiro[4.5]decane‐1,3‐diones
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2024-10-29 , DOI: 10.1002/adsc.202401169
Arup Bhowmik, Koushik Naskar, Shantonu Roy, Abhishek Sahoo, Indubhusan Deb

The C(sp3)‐H functionalization via intramolecular hydride transfer initiated cascade annulation for the synthesis of spiro‐fused succinimide‐containing tetrahydroquinolines induced by iminium intermediates is described. A series of diastereoselective 2,7‐diazaspiro[4.5]decanes‐1,3‐diones were achieved using ortho‐amino‐benzylidene‐succinimide using Lewis acid catalysis. This scandium triflate Sc(OTf)3 catalysed, oxidant‐free protocol leads to the diastereoselective synthesis of a class of 2,7‐diazaspiro[4.5]decanes‐1,3‐diones derivatives with 48‐98% yield in a single step.

中文翻译:


通过 C(sp3)-H 键官能化进行非对映选择性分子内螺环化,合成 2,7-重氮二氮氧代[4.5]癸烷-1,3-二酮



描述了通过分子内氢化物转移启动的级联环化,用于合成由亚胺中间体诱导的含螺体熔融的含琥珀酰亚胺的四氢喹啉的 C(sp3)-H 官能化。使用 Lewis 酸催化使用邻氨基-苄基-琥珀酰亚胺实现了一系列非对映选择性 2,7-二氮杂螺[4.5]癸烯-1,3-二酮。这种三氟甲酸钪 Sc(OTf)3 催化的无氧化剂方案导致一类 2,7-二氮螺[4.5]癸烷-1,3-二酮衍生物的非对映选择性合成,一步中产率为 48-98%。
更新日期:2024-10-29
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