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C−N Axial Chiral Hypervalent Iodine Reagents: Catalytic Stereoselective α‐Oxytosylation of Ketones
Author(s) -
Alharbi Haifa,
Elsherbini Mohamed,
Qurban Jihan,
Wirth Thomas
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202005253
Subject(s) - hypervalent molecule , stereoselectivity , propiophenone , chemistry , reagent , catalysis , iodine , aniline , chiral auxiliary , combinatorial chemistry , organic chemistry , enantioselective synthesis , ketone
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.