Enantioselective gold catalyzed cascade construction of pyrroloindoline derivatives

A new method was developed to enantioselectively synthesize pyrroloindolines from the reaction of allenoamides with tryptamines by using BINOL derived phosphoramidate ligated gold catalyst. Electrophilic addition of the gold-allene complex led to tryptamine's C-3-dearomatization, which, followed by C-2 cyclization, provided the desired annulation product. In addition, furoindoline product could also be prepared from the reaction of tryptol. (C) 2015 Elsevier Ltd. All rights reserved.