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Asymmetric N-aminoalkylation of 3-substituted indoles by N-protected N,O-acetals: an access to chiral propargyl aminals

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Abstract

A direct enantioselective N1 aminoalkylation of 3-substituted indoles is efficiently catalyzed by a phosphoric acid catalyst under mild conditions to afford diverse enantioenriched propargyl aminals. The strategy could be applied to the modification of tryptophan containing oligopeptides. Additionally, structurally diverse and multifunctional transformations of the propargyl aminal products reveal the potential synthetic utility of this protocol.

Graphical abstract: Asymmetric N-aminoalkylation of 3-substituted indoles by N-protected N,O-acetals: an access to chiral propargyl aminals

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Article information


Submitted
17 Apr 2020
Accepted
14 May 2020
First published
15 May 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Asymmetric N-aminoalkylation of 3-substituted indoles by N-protected N,O-acetals: an access to chiral propargyl aminals

J. Yang, Z. He, L. Hong, W. Sun and R. Wang, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00795A

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