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Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.

ABSTRACT: The hydroamination of internal alkynes via tandem rhodium catalysis gives branched N-allylic indolines with high regio- and enantioselectivity. An acid switch provides access to the linear isomer in preference to the branched isomer by an isomerization mechanism. Mechanistic studies suggest formation of an allene intermediate, which undergoes hydroamination to generate allylic amines instead of the enamine or imine products typically observed in alkyne hydroaminations.

SUBMITTER: Chen QA

PROVIDER: S-EPMC4870006 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature

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Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.

Chen Qing-An QA Chen Zhiwei Z Dong Vy M VM

Journal of the American Chemical Society 20150629 26

The hydroamination of internal alkynes via tandem rhodium catalysis gives branched N-allylic indolines with high regio- and enantioselectivity. An acid switch provides access to the linear isomer in preference to the branched isomer by an isomerization mechanism. Mechanistic studies suggest formation of an allene intermediate, which undergoes hydroamination to generate allylic amines instead of the enamine or imine products typically observed in alkyne hydroaminations. ...[more]

PMID: 26107923

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