Oxidative Pictet-Spengler cyclisations through acceptorless iridium-catalysed dehydrogenation of tertiary amines

Tetrahedron
2021.0

Abstract

The valuable tetrahydro-β- and γ-carboline skeleta can be accessed through Pictet-Spengler cyclisation initiated by acceptorless dehydrogenation of saturated cyclic amines. The substrate scope for the β-isomers is found to be somewhat limited, but access to the γ-isomers through the more reactive 2-(aminoethyl)indoles is more general. The synthetic utility of hydrogen transfer catalysis is highlighted in a two-step preparation of the alkaloid desbromoarborescidine A by sequential redox-neutral alkylation/dehydrogenative cyclisation. © 2020 Elsevier Ltd

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