1. Department of Chemistry, University of Utah, 315 S 1400 E, Salt Lake City, Utah, 84112 USA
These authors contributed equally to this work.;2. Department of Chemistry, University of Utah, 315 S 1400 E, Salt Lake City, Utah, 84112 USA
Abstract:
A palladium-catalyzed enantioselective redox-relay Heck reaction of 2-indole triflates and disubstituted alkenes is reported. This process combines readily available indole triflates with a variety of alkenes to afford a range of indole derivatives bearing a stereocenter adjacent to C2. Enantioselectivity is achieved through use of a simple pyridine-oxazoline ligand. Tuning the electronics of the indole, through judicious choice of N-protecting group, is required to ensure selective β-hydride elimination away from the indole core. Utility of this method is highlighted in a modular formal synthesis of an S1P1 agonist precursor developed by Merck.