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Redox-triggered dearomative [5 + 1] annulation of indoles with <i>O</i>-alkyl <i>ortho</i>-oxybenzaldehydes for the synthesis of spirochromanes

Lianyi Cao, Fangzhi Hu, Hongmei Sun, Xiaomei Zhang, Shuai‐Shuai Li

2022Organic Chemistry Frontiers30 citationsDOI

Abstract

The dearomative [5 + 1] annulation of 2-methylindoles with new five-membered synthon was developed through cascade [1,5]-hydride transfer/dearomative cyclization in HFIP for the synthesis of spirochromanes bearing the 2-methylindolenine skeleton.

Topics & Concepts

ChemistryAnnulationSynthonHydrideCascadeAlkylMedicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryCatalysisChromatographyHydrogenSynthesis of Indole DerivativesCatalytic C–H Functionalization MethodsAxial and Atropisomeric Chirality Synthesis
Redox-triggered dearomative [5 + 1] annulation of indoles with <i>O</i>-alkyl <i>ortho</i>-oxybenzaldehydes for the synthesis of spirochromanes | Litcius