Synthesis of tetrahydro-β-carbolines via isomerization of N-allyltryptamines: a metal-catalyzed variation on the Pictet–Spengler theme

An efficient and broadly applicable alternative to the classical Pictet–Spengler synthesis of tetrahydro-β-carbolines is presented. The method relies on metal-catalyzed isomerization of allylic amines to form reactive iminium intermediates which can be trapped by a tethered indole nucleophile. Original language English Journal Chemical Communications Volume 48 Issue number 27 Pages (from-to) 3345-3347 ISSN 1359-7345 DOIs https://doi.org/10.1039/c2cc17704h Publication status Published - 2012 Bibliographical note Electronic supplementary information (ESI) available: Experimental procedures, characterization data for all substrates and products. See DOI: 10.1039/c2cc17704h