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色胺衍生异腈与碘鎓叶立德的偶联-螺环化串联反应及开环反应

Coupling-Spirocyclization Cascade of Tryptamine-Derived Isocyanides with Iodonium Ylides and Despirocyclization Reactions.

作者信息

Yuan Luo-Rong, Ji Shun-Jun, Xu Xiao-Ping

机构信息

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, People's Republic of China.

Suzhou Baolidi Functional Materials Research Institute, Suzhou 215144, People's Republic of China.

出版信息

Org Lett. 2023 Nov 3;25(43):7858-7862. doi: 10.1021/acs.orglett.3c03090. Epub 2023 Oct 20.

DOI:10.1021/acs.orglett.3c03090
PMID:37862138
Abstract

A cobalt(II)-catalyzed coupling-cyclization cascade reaction between tryptamine-derived isocyanides and iodonium ylides is investigated, which allowed for the synthesis of different types of spiroindoline compounds by variation of substituents at the N1- and C2-positions in the indole skeleton. More interesting is that the spiroindoline products could undergo despirocyclization in the presence of amines, enabling efficient construction of enamine compounds.

摘要

研究了钴(II)催化的色胺衍生异腈与碘鎓叶立德之间的偶联-环化串联反应,该反应通过改变吲哚骨架中N1-和C2-位的取代基,实现了不同类型螺吲哚啉化合物的合成。更有趣的是,螺吲哚啉产物在胺存在下可发生螺环开环反应,从而能够高效构建烯胺化合物。

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引用本文的文献

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Shining light on tryptamine-derived isocyanides: access to constrained spirocylic scaffolds.聚焦色胺衍生的异腈:通往受限螺环骨架的途径。
Chem Sci. 2024 Apr 8;15(18):6867-6873. doi: 10.1039/d3sc06304f. eCollection 2024 May 8.