有机分子催化立体选择性反应合成含氟杂环的研究

项目名称： 有机分子催化立体选择性反应合成含氟杂环的研究

项目编号： No.21272153

项目类型： 面上项目

立项/批准年度： 2013

项目学科： 数理科学和化学

项目作者： 宋力平

作者单位： 上海大学

项目金额： 80万元

中文摘要： 含单氟和三氟甲基的杂环化合物因其具有特殊的生理活性，其合成方法是当今的一个研究热点。与直接氟化相比，砌块法克服了反应条件苛刻、选择性差等缺点，从而具有反应条件温和，选择性好等优点而愈受重视。另一方面，手性有机分子催化剂由于具有简单易得、在无金属催化剂的环境中并在相对温和的反应条件下具有很好的对映选择性等优点，最近越来越受化学家的关注。在具有对映选择性的催化体系中，不对称有机分子催化体系被认为是除了生物催化、金属催化以外的第三种重要的催化体系，在有机合成中应用越来越广。本项目的提出结合了含氟砌块法和不对称有机分子催化剂具有高的立体选择性的特点，研究不对称有机分子催化剂催化含氟底物的反应性能，在现有工作的基础上，以期合成一系列含单氟或含三氟甲基具有立体选择性的含氟杂环化合物，并进一步拓展不对称有机分子催化剂在催化含氟底物的一锅法、多组分立体选择性反应中的应用.

中文关键词： 单氟杂环；三氟甲基杂环；立体化学；有机小分子；

英文摘要： The synthetic methods for preparation of monofluorinated or trifluormethylated heterocycles has received much attention since the fluorine-containing heterocycles usually show interesting biological activities with potential for applications in the medicinal and agricultural fields. Compared with the directed fluorination, the fluorinated building-block strategy has received increasing interest due to their mild reaction conditions with highly selectivity. On the other hand,the use of small chiral organic molecules as enantioselective catalysts, with the associated advantages of their easy availability and of carrying out asymmetric transformations in a metal free-environment and under mild and simple reaction conditions, has lately experienced an impressive growth. Therefore, asymmetric organocatalysis is now considered the "third pillar" of enantioselective catalysis, together with biocatalysis and metal catalysis, and is being increasingly used in organic synthesis. This project focuses on the study of the asymmetric reactions involving the fluorinated substrates catalyzed by asymmetric organocatalysts. Thus, a series of monofluorinated or trimethylfluorinated heterocycles with stereoselectivity are expected to be obtained, based on our recent investigations. Moreover, the stereoselective MCRs involving the f

英文关键词： Mono-fluorinated heterocycle；Ttrifluoromethylated heterocycle；Stereochemistry；Organocatalysis；