Highly enantioselective CH oxidation of vic-Diols with Shi's oxazolidinone dioxiranes.
[reaction: see text] Through an analogical study of the transition states of CH oxidation and asymmetric epoxidation of terminal alkenes, the first dioxirane-mediated catalytic highly enantioselective CH oxidation method was realized with Shi's oxazolidinone ketone derivatives. Very good enantioselectivity (up to 92% ee) may be obtained for both asymmetrization of meso vic-diols and kinetic resolution of racemic vic-diols.
Jakka
Kavitha
K
Department of Chemistry, University of Texas at San Antonio, 78249-0698, USA.
Zhao
Cong-Gui
CG
D000438:Alcohols / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000438:Alcohols; D000475:Alkenes; D004852:Epoxy Compounds; D010080:Oxazoles; C061799:dioxirane