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Synthesis
DOI: 10.1055/a-2515-0296
DOI: 10.1055/a-2515-0296
feature
Enantioselective Synthesis of N-Alkylated Indoles Enabled by Nickel-Catalyzed C(sp3 )–C(sp3 ) Coupling
The authors are grateful to the National Natural Science Foundation of China (22101250 and 22371247), the Yunnan Fundamental Research Projects (202301AW070005), the Project of Innovative Research Team of Yunnan Province (202405AS350010), and the Yunnan Revitalization Talent Support Program (XDYC-QNRC-2022-0696) for financial support.
Abstract
Although considerable efforts have been made to construct chiral functionalized indoles, catalytic and efficient methods to access a diverse range of chiral N-alkylated indoles bearing a stereocenter with two minimally different alkyl groups at the N-1 position from readily accessible substrates remain limited. Here, we describe a modular Ni-catalyzed C(sp3 )–C(sp3 ) cross-coupling strategy that couples an array of N-indolyl-substituted alkenes with alkyl iodides to yield chiral α,α-dialkyl indoles in single regioisomeric form, in up to 90% yield and 99% ee.
Key words
asymmetric catalysis - nickel catalysis - C(sp3 )–C(sp3 ) cross-coupling - indole - alkylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2515-0296.
- Supporting Information
Publication History
Received: 14 November 2024
Accepted after revision: 11 January 2025
Accepted Manuscript online:
11 January 2025
Article published online:
19 February 2025
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