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Regioselective Photoredox Catalyzed Cycloadditions of Acyclic Carbonyl Ylides

07 June 2024, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

A photoredox catalyzed [3+2] dipolar cycloaddition between acyclic carbonyl ylides generated from š¯›¼-cyano epoxides and dipolarophiles is described. This method, influenced by anionic charge localization and temperature control, enabled the synthesis of regioselective functionalized cyclic ethers. By leveraging different dipolarophiles, Lewis acid mediated activation afforded either furan or hydroxy-dihydronaphthalene scaffolds. A direct synthesis of lignan natural products isodiphyllin and diphyllin is achieved by exploiting the nitrileā€™s reactivity as a directing handle for the desired regioisomer.

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Version History

Jun 07, 2024 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2024-k035t
D O I: 10.26434/chemrxiv-2024-k035t [opens in a new tab]

Authorā€™s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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