An-PIQ催化的β-碘代Morita-Baylis-Hillman加合物动力学拆分研究  

An-PIQ Catalyzed Kinetic Resolution of β-Iodo Morita-Baylis-Hillman Adducts

作　　者：朱明玉[1] 邓卫平[1] 

机构地区：[1]华东理工大学药学院上海市功能性材料化学重点实验室,上海200237

出　　处：《有机化学》2016年第10期2397-2406,共10页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21372074)资助项目~~

摘　　要：β-碘代Morita-Baylis-Hillman(MBH)加合物作为一种多官能团的手性砌块,是多种天然产物和药物分子的重要中间体.以课题组最近开发的An-PIQ为亲核催化剂,首次利用非酶亲核酰化动力学拆分的方法获得了一系列高光学纯β-碘代MBH加合物,S值最高可达165.该方法不仅解决了脂肪醛衍生的MBH加合物二级醇在动力学拆分中的低选择性问题,而且具有条件温和,较好的底物普适性,并能放大到克级规模等特点.Chiral β-iodo Morita-Baylis-Hillman （MBH） adducts are important versatile synthetic building blocks for many nat-ural products and drug molecules. By using a recently developed acyl transfer catalyst An-PIQ, the kinetic resolutions of a series of β-iodo MBH adducts were investigated, providing the recovered alcohols in good yields with high enantioselectivities （up to 99.9% ee） and good selectivity factors （S up to 165）. This method overcomes the issue of low selectivity confronted in the kinetic resolution of aliphatic aldehyde-derived MBH adducts as secondly alcohols, and features mild reaction conditions, broad sub-strate scope, and easy scaling-up to gram scale.

关 键 词：β-碘代MBH加合物 亲核催化 对映选择性 动力学拆分 

分 类 号：O621.251[理学—有机化学]