Enantioselective N Alkylation of Indoles via an Intermolecular Aza Wacker Type Reaction.
The development of an intermolecular and enantioselective aza Wacker reaction is described. Using indoles as the N source and a selection of alkenols as the coupling partners selective b hydride elimination toward the alcohol was achieved. This strategy preserves the newly formed stereocenter by preventing the formation of traditionally observed enamine products. Allylic and homoallylic alcohols with a variety of functional groups are compatible with the reaction in high enantioselectivity. Isotopic labeling experiments support a syn amino palladation mechanism for this new class of aza Wacker reactions.
Journal of the American Chemical Society