American Chemical Society
ja9b01476_si_002.pdf (42.29 MB)

Enantioselective N‑Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction

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journal contribution
posted on 2019-05-22, 00:00 authored by Jamie R. Allen, Ana Bahamonde, Yukino Furukawa, Matthew S. Sigman
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 β-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.