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Palladium-catalysed imidoylative spirocyclization of 3-(2-isocyanoethyl)indoles
Chemical Communications ( IF 4.9 ) Pub Date : 2021-09-16 , DOI: 10.1039/d1cc03240b
Shi Tang 1 , Shumin Ding 2 , Dan Li 2 , Lianjie Li 2 , Haixia Zhao 2 , Minxue Chai 2 , Jian Wang 2
Affiliation  

A palladium-catalysed construction of spiroindolines through dearomative spirocyclization of 3-(2-isocyanoethyl)indoles has been developed. 2′-Aryl-, vinyl-, and alkyl-substituted spiroindolines could be accessed under mild conditions with excellent functional group tolerance. C1-tethered oxindole- and indole-spiroindoline bisheterocycles were generated in high yields via alkene/allene insertion and an imidoylative spirocyclization cascade. Additionally, a tandem dearomatization of two different indoles was realized with N-(2-bromobenzoyl)indoles as the electrophilic coupling partner of 3-(2-isocyanoethyl)indoles, affording polyindoline spiroindoline bisheterocyclic scaffolds conveniently. Under the catalysis of Pd(OAc)2 and a spinol-derived phosphoramidite ligand, chiral spiroindolines were successfully accessed with up to 95% yield and 85% ee.

中文翻译:

钯催化的 3-(2-异氰乙基)吲哚的亚胺酰化螺环化

钯催化的螺二氢吲哚通过 3-(2-异氰乙基) 吲哚的脱芳环化反应被开发出来。2'-芳基-、乙烯基-和烷基-取代的螺二氢吲哚可以在温和条件下获得,具有优异的官能团耐受性。C1-tethered oxindole-和 indole-spiroindoline bisheterocycles通过烯烃/丙二烯插入和亚氨基化螺环化级联以高产率生成。此外,利用N- (2-溴苯甲酰基)吲哚作为3-(2-异氰乙基)吲哚的亲电偶联伙伴实现了两种不同吲哚的串联脱芳构化,方便地提供了聚二氢吲哚-螺二氢吲哚双杂环支架。在Pd(OAc) 2的催化下 和衍生自旋旋醇的亚磷酰胺配体,手性螺二氢吲哚以高达 95% 的产率和 85% 的 ee 成功获得。
更新日期:2021-09-24
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