Jakka Kavitha, Zhao Cong-Gui
Department of Chemistry, University of Texas at San Antonio, 78249-0698, USA.
Org Lett. 2006 Jul 6;8(14):3013-5. doi: 10.1021/ol060904a.
[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.
[反应:见正文] 通过对CH氧化和末端烯烃不对称环氧化过渡态的类比研究,利用Shi恶唑烷酮酮衍生物实现了首例二氧杂环丙烷介导的催化高对映选择性CH氧化方法。对于内消旋邻二醇的不对称化和外消旋邻二醇的动力学拆分,均可获得非常好的对映选择性(高达92% ee)。