ASYMMETRIC EPOXIDATION OF OLEFINS BY CHIRAL DIOXIRANES

描述：拟议研究的总体目标是开发新的、 手性二氧六环高效催化不对称环氧化烯烃 氧酮(过氧单硫酸钾)和手性酮原位生成 并将该方法应用于生物活性化合物的合成。 新方法将被开发来满足几个重要的标准， 包括简单性、通用性、灵活性、高对映选择性和 低毒。这些标准中的每一个都对适用性非常重要 本发明涉及生物活性化合物的合成方法。 拟议研究的具体目标是：(1)综合各种类型的 从容易获得的手性起始材料中提取的手性酮，例如 碳水化合物，并测试这些手性酮用于 通过二氧六环进行的不对称环氧化反应；(2)了解反应机理和 手性环氧乙烷催化烯烃不对称环氧化反应的影响因素 (3)确定所需的酮催化剂的关键结构元素 高的不对称诱导，并随后开发了一种酮催化剂 高稳定性、高活性和对映选择性；(4)应用新的 不对称环氧化反应在生物活性合成中的应用 具有生物活性的化合物和有用的手性构筑块 化合物。

DESCRIPTION: The overall goal of the proposed research is to develop new, efficient, catalytic asymmetric epoxidation of olefins by chiral dioxirane generated in situ from Oxone (potassium peroxymonosulfate) and chiral ketone and to apply this method to the synthesis of biologically active compounds. The new method will be developed to meet several important criteria, including simplicity, generality, flexibility, high enantioselectivity, and low toxicity. Each of these criteria is very important to the applicability of the method to the synthesis of biologically active compounds. The specific aims of the proposed research are: (1) to synthesize various chiral ketones from readily available chiral starting materials, such as carbohydrates and to test the feasibility of these chiral ketones for asymmetric epoxidation via dioxiranes; (2) to understand the mechanism and factors involved in asymmetric epoxidation of olefin by chiral dioxirane; (3) to identify the key structural elements of ketone catalyst required for high asymmetric induction and subsequently develop a ketone catalyst with high stability, reactivity, and enantioselectivity; (4) to apply the newly developed asymmetric epoxidation to the synthesis of biologically active compounds and useful chiral building blocks towards biologically active compounds.