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Lanthanide Silylamide-Catalyzed Synthesis of Pyrano[2,3-<i>b</i>]indol-2-ones

Qi‐Fa Chen, Yue Teng, Fan Xu

2021Organic Letters21 citationsDOI

Abstract

A lanthanide silylamide-catalyzed tandem reaction of isatins, diethyl phosphite, and 2,3-diarylcyclopropenones has been developed. A series of pyrano[2,3-b]indol-2-ones were synthesized in high yields. The cooperation of the Lewis acidity of the lanthanide center and the Bronsted basicity of the N(SiMe3)2 anion may be the key factor affecting the catalytic activity of lanthanide amides.

Topics & Concepts

LanthanideChemistryCatalysisTandemMedicinal chemistryBrønsted–Lowry acid–base theoryOrganic chemistryCombinatorial chemistryIonMaterials scienceComposite materialAsymmetric Synthesis and CatalysisCyclopropane Reaction MechanismsSynthetic Organic Chemistry Methods