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

Junxian Yang; Zeyuan He; Liang Hong; Wangsheng Sun; Rui Wang

doi:10.1039/D0OB00795A

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

Junxian Yang,^a Zeyuan He,^a Liang Hong,

^b Wangsheng Sun

*^a and Rui Wang

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Pharmacology, School of Basic Medical Sciences & Research Unit of Peptide Science, Chinese Academy of Medical Sciences, 2019RU066, Lanzhou University, Lanzhou 730000, China
E-mail: sunws@lzu.edu.cn, wangrui@lzu.edu.cn

^b Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China

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.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/D0OB00795A
Article type: Communication
Submitted: 17 Apr 2020
Accepted: 14 May 2020
First published: 15 May 2020

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Org. Biomol. Chem., 2020,18, 4169-4173

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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, 18, 4169 DOI: 10.1039/D0OB00795A

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Organic & Biomolecular Chemistry

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

Abstract

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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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