53243-96-2Relevant academic research and scientific papers
A new target for highly stereoselective Katsuki-Sharpless epoxidation - One-pot synthesis of C2-symmetric 2,2′-bioxiranes
Bilenko, Vitaliy,Jiao, Haijun,Spannenberg, Anke,Fischer, Christine,Reinke, Helmut,Koesters, Jutta,Komarov, Igor,Boerner, Armin
, p. 758 - 767 (2008/02/07)
The double asymmetric Katsuki-Sharpless epoxidation of a conjugated diallyl alcohol affords excellent enantioselectivity (>97% ee), the product being isolated as the stable p-nitrobenzoate 5a or tosylate 5b. The optical purities of the chiral epoxides were determined by HPLC on chiral columns, while the molecular structures of compounds 5a and 7 and the absolute configuration of mono-epoxide 12 were confirmed by X-ray crystallography. Possible π-π stacking interaction has been evaluated by ab initio calculation. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
