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Strain-enabled radical spirocyclization cascades: rapid access to spirocyclobutyl lactones and - lactams

Das, K and Pedada, A and Singha, T and Hari, DP (2023) Strain-enabled radical spirocyclization cascades: rapid access to spirocyclobutyl lactones and - lactams. In: Chemical Science .

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Official URL: https://doi.org/10.1039/d3sc05700c


Spirocyclobutane derivatives have gained significant attention in drug discovery programs due to their broad spectrum of biological activities and clinical applications. Ring-strain in organic molecules is a powerful tool to promote reactivity by releasing strain energy, allowing the construction of complex molecules selectively and efficiently. Herein, we report the first strain-enabled radical spirocyclization cascades for the synthesis of functionalized spirocyclobutyl lactones and - lactams, which are finding increasing applications in medicinal chemistry. The reaction of interelement compounds with bicyclobutane (BCB) allyl esters and - amides proceeds with high chemoselectivity under simple, catalyst-free conditions using blue light irradiation. The reaction has been successfully extended to synthesize bis-spirocycles. To introduce a more diverse set of functional groups, we have developed a dual photoredox/nickel catalytic system capable of mediating the carbosulfonylation of BCB allyl amides. The reaction shows broad applicability across various (hetero)aryl halides, aryl sulfinates, and BCB allyl amides, operates under mild conditions and demonstrates excellent functional group compatibility. The functional groups introduced during the cascade reactions served as versatile handles for further synthetic elaboration. © 2024 The Royal Society of Chemistry.

Item Type: Journal Article
Publication: Chemical Science
Publisher: Royal Society of Chemistry
Additional Information: The copyright for this article belongs to Author.
Keywords: Application programs; Esters; Molecules; Strain energy, Broad spectrum; Clinical application; Complex molecules; Condition; Drug discovery; Functionalized; Medicinal chemistry; Organic molecules; Ring strains; Spirocyclization, Amides
Department/Centre: Others
Date Deposited: 01 Mar 2024 10:35
Last Modified: 01 Mar 2024 10:35
URI: https://eprints.iisc.ac.in/id/eprint/84071

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