Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

Authors

Melanie A. Drew, University of WollongongFollow
Sebastian Arndt, Heidelberg University
Christopher Richardson, University of WollongongFollow
Matthias Rudolph, Heidelberg University
A. Stephen K. Hashmi, Ruprecht-Karls-University Heidelberg
Christopher J. T Hyland, University of WollongongFollow

RIS ID

140314

Publication Details

Drew, M. A., Arndt, S., Richardson, C., Rudolph, M., Hashmi, A. K. & Hyland, C. J.T. (2019). Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics. Chemical Communications, 55 (93), 13971-13974.

Abstract

Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.

Grant Number

ARC/DP180100904