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

ABSTRACT: 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 ?-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.

SUBMITTER: Allen JR

PROVIDER: S-EPMC6583780 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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

Allen Jamie R JR Bahamonde Ana A Furukawa Yukino Y Sigman Matthew S MS

Journal of the American Chemical Society 20190524 22

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. Isot ...[more]

PMID: 31117643

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