Divergent Synthesis of Pentacyclic Isoindolinones Enabled by Sequential Insertion of Two Different Isocyanides and Acid Promoted Cyclization of Ketenimines,Organic Letters

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Divergent Synthesis of Pentacyclic Isoindolinones Enabled by Sequential Insertion of Two Different Isocyanides and Acid Promoted Cyclization of Ketenimines
Organic Letters ( IF 4.9 ) Pub Date : 2023-03-22 , DOI: 10.1021/acs.orglett.3c00393
Yi-Ming Zhu ₁ , Xiao-Ping Xu _{1,

2} , Shun-Jun Ji _{1,

3}

Affiliation

A palladium-catalyzed multicomponent reaction involving o-bromobenzaldehydes and two different isocyanides was developed to assemble series of isoindolinones with spiroindolenine or azepinoindole skeletons. This sequential insertion reaction features mild conditions, a wide substrate scope, and high efficiency. Preliminary mechanistic study indicated that the difference in steric hindrance between isocyanide components is crucial when regulating the reaction sequence, whereas the ligand also played an important role during the whole process.

中文翻译：

通过顺序插入两种不同的异氰化物和酸促进酮亚胺的环化实现五环异吲哚啉酮的发散合成

开发了一种涉及邻溴苯甲醛和两种不同异氰化物的钯催化多组分反应，以组装一系列具有螺吲哚啉或氮杂吲哚骨架的异吲哚啉酮。这种顺序插入反应具有条件温和、底物范围广、效率高的特点。初步的机理研究表明，异氰化物组分之间空间位阻的差异在调节反应顺序时至关重要，而配体在整个过程中也起着重要作用。

更新日期：2023-03-22

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