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C−N axial chiral hypervalent iodine reagents: catalytic stereoselective α‐oxytosylation of ketones

Alharbi, Haifa, Elsherbini, Mohamed, Qurban, Jihan and Wirth, Thomas 2021. C−N axial chiral hypervalent iodine reagents: catalytic stereoselective α‐oxytosylation of ketones. Chemistry - A European Journal 27 (13) , pp. 4317-4321. 10.1002/chem.202005253

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Abstract

A simple synthesis of a library of novel C−N axially chiral iodoarenes is achieved in a three‐step synthesis from commercially available aniline derivatives. C−N axial chiral iodine reagents are rarely investigated in the hypervalent iodine arena. The potential of the novel chiral iodoarenes as organocatalysts for stereoselective oxidative transformations is assessed using the well explored, but challenging stereoselective α‐oxytosylation of ketones. All investigated reagents catalyse the stereoselective oxidation of propiophenone to the corresponding chiral α‐oxytosylated products with good stereochemical control. Using the optimised reaction conditions a wide range of products was obtained in generally good to excellent yields and with good enantioselectivities.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Additional Information: This is an open access article under the terms of the Creative Commons Attribution License
Publisher: Wiley
ISSN: 0947-6539
Funders: The Government of Saudi Arabia and the Northern Borders University, KSA
Date of First Compliant Deposit: 9 February 2021
Date of Acceptance: 11 January 2021
Last Modified: 03 Aug 2022 01:48
URI: https://orca.cardiff.ac.uk/id/eprint/138383

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