93397-58-1Relevant articles and documents
C?N Axial Chiral Hypervalent Iodine Reagents: Catalytic Stereoselective α-Oxytosylation of Ketones
Alharbi, Haifa,Elsherbini, Mohamed,Qurban, Jihan,Wirth, Thomas
supporting information, p. 4317 - 4321 (2021/02/16)
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.
Enantioselective α-tosyloxylation of ketones catalyzed by spirobiindane scaffold-based chiral iodoarenes
Yu, Jun,Cui, Jian,Hou, Xue-Sen,Liu, Shan-Shan,Gao, Wen-Chao,Jiang, Shan,Tian, Jun,Zhang, Chi
scheme or table, p. 2039 - 2055 (2012/03/11)
Enantiomerically pure iodoarene (S)-2 and its derivatives (S)-3 to (S)-18 with a spirobiindane scaffold have been synthesized. The evaluation of these new chiral iodoarenes as catalysts in the enantioselective α-tosyloxylation of ketones was performed using m-CPBA as a stoichiometric oxidant, and the synthetically useful α-tosyloxylated ketones were obtained in up to 58% enantiomeric excess (ee).
