Burke Christopher P, Shi Yian
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
J Org Chem. 2007 May 25;72(11):4093-7. doi: 10.1021/jo070205r. Epub 2007 Apr 26.
This paper describes a highly chemo- and enantioselective epoxidation of conjugated cis-enynes using readily available glucose-derived ketone 2 as catalyst and Oxone as oxidant to form cis-propargyl epoxides in high ee's. The interaction between the alkyne group of the substrate and the oxazolidinone moiety of the ketone catalyst as well as the interactions between the substituents on enynes and the oxazolidinone moiety of the ketone catalyst are important for the stereodifferentiation.
本文描述了一种使用易于获得的葡萄糖衍生酮2作为催化剂、过硫酸氢钾复合盐作为氧化剂，对共轭顺式烯炔进行高度化学选择性和对映选择性环氧化反应，以高对映体过量（ee值）生成顺式炔丙基环氧化物。底物的炔基与酮催化剂的恶唑烷酮部分之间的相互作用以及烯炔上的取代基与酮催化剂的恶唑烷酮部分之间的相互作用对于立体分化很重要。
