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Rhodium-Catalyzed Enantioselective Hydroamination Of Alkynes With Indolines.

Q. Chen, Z. Chen, V. M. Dong
Published 2015 · Chemistry, Medicine

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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.
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