The 1,2,3,4-tetrahydro-�-carboline (THBC) ring system is a key structural element in a range of biologically and pharmacologically important alkaloids isolated from a variety of natural sources. THBCs are traditionally synthesized via the Pictet�Spengler reaction, where tryptamines are condensed with aldehydes under acidic conditions. Herein we report an efficient and broadly applicable alternative to the classical Pictet�Spengler synthesis. The method relies on metal-catalyzed isomerization of allylic amines to form reactive iminium intermediates, which can be trapped by tethered indoles.

Metal-catalyzed variations on the Pictet-Spengler theme

245th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.