Rhodium-catalyzed pyridannulation of indoles with diazoenals: a direct approach to pyrido[1,2-a]indoles?

Organic & Biomolecular Chemistry Pub Date: 2016-03-03 DOI: 10.1039/C6OB00360E

Abstract

A novel rhodium catalyzed pyridannulation of 3-substituted indoles with diazoenals furnished privileged pyrido[1,2-a]indoles. The reaction is proposed to involve a [4 + 2]-annulation of the diacceptor rhodium enalcarbenoid via C-2 functionalization of the indole. The utility of the methodology was demonstrated with a short synthesis of the tetrahydropyrido[1,2-a]indole core, present in a large number of biologically important polycyclic indole alkaloids.

Graphical abstract: Rhodium-catalyzed pyridannulation of indoles with diazoenals: a direct approach to pyrido[1,2-a]indoles
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