Oxidative rearrangement of alkynes to chiral α-arylalkanoic esters

Alkahtani, Rawiyah, Westphäling, Johannes, Gorecka, Aleksandra, Babaahmadi, Rasool, Gieman, Hanaa Hussien M, Finance, Maylis, Lorente-Martinez, Jaime, Bhattacherjee, Dhananjay, Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831, Baik, Mu-Hyun and Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 2025. Oxidative rearrangement of alkynes to chiral α-arylalkanoic esters. Chemical Science 10.1039/d5sc07882b

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Abstract

Chiral α-arylalkanoic esters, valued as anti-inflammatory agents, are synthesised through an enantioselective oxidative rearrangement of alkynes under green, metal-free conditions. This study achieves this transformation using chiral iodine(iii) reagents with para-toluenesulfonic acid and various alcohols, producing the esters in up to 91% yield and 99% enantiomeric excess. The scope of the reaction particularly includes electron-rich non-terminal arylalkynes. Density functional theory calculations give insight into the origin of enantioselectivities of this process.

Item Type:	Article
Date Type:	Published Online
Status:	In Press
Schools:	Schools > Chemistry Research Institutes & Centres > Cardiff Catalysis Institute (CCI)
Additional Information:	License information from Publisher: LICENSE 1: URL: https://creativecommons.org/licenses/by/3.0/, Start Date: 2025-11-19
Publisher:	Royal Society of Chemistry
ISSN:	2041-6520
Date of First Compliant Deposit:	4 December 2025
Date of Acceptance:	17 November 2025
Last Modified:	05 Dec 2025 14:54
URI:	https://orca.cardiff.ac.uk/id/eprint/182900

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