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Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes |
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| Authors: | Dr Huaiyuan Zhang Prof?Dr Rodrigo A Cormanich Prof?Dr Thomas Wirth |
| Institution: | 1. School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff, CF10 3AT UK
Lanzhou Petrochemical University of Vocational Technology, Lanzhou, 730060 P. R. China;2. Institute of Chemistry, University of Campinas, Campinas, Sao Paulo, 13083-862 Brazil;3. School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff, CF10 3AT UK |
| Abstract: | Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents. |
| Keywords: | binaphthyl ligands iodine(III) reagents ligand synthesis oxidation stereoselective synthesis |