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DOI: 10.1055/a-2680-2438
Xanthate-Based Radical Addition/Spirocyclization on C2-Substituted Tryptamine-Derived Isonitriles
Authors
Funding Information Financial support from CONAHCYT (Project CBF2023-2024-2227) is gratefully acknowledged.
Abstract
A metal-free protocol for constructing spiroindolines via a radical cascade process is reported. The reaction cascade comprises a radical intermolecular addition to a tryptamine-derived isonitrile, followed by spirocyclization of the intermediate radical onto the C-3 position of the indole system, and concluding with a final oxidation step. Introducing a malonyl or acetoxyl group at the C-2 position of the indole system, along with the addition of a radical bearing an electron-withdrawing group, facilitated the formation of the enamine products. The use of the xanthate-mediated chemistry enabled the generation of primary and secondary electrophilic radicals derived from esters, nitriles, ketones, and lactones.
Publication History
Received: 08 May 2025
Accepted after revision: 08 August 2025
Accepted Manuscript online:
08 August 2025
Article published online:
09 September 2025
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