C−N Axial Chiral Hypervalent Iodine Reagents: Catalytic Stereoselective α-Oxytosylation of Ketones

Haifa Alharbi, Mohamed Elsherbini, Jihan Qurban, Thomas Wirth

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)4317-4321
Number of pages5
JournalChemistry - A European Journal
Volume27
Issue number13
Early online date11 Jan 2021
DOIs
Publication statusPublished - 1 Mar 2021

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