ASYMMETRIC EPOXIDATION OF OLEFINS BY CHIRAL DIOXIRANES

描述：拟议研究的总体目标是开发新的， 通过手性二环氧乙烷的烯烃的有效催化不对称环氧化 由过硫酸氢钾（过一硫酸钾）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。 新方法的开发将满足几个重要标准， 包括简单性、通用性、灵活性、高对映选择性， 低毒性。 这些标准中的每一个都对适用性非常重要。 的方法来合成生物活性化合物。 本研究的具体目标是：（1）综合各种 由容易获得的手性起始原料，例如 碳水化合物，并测试这些手性酮用于 通过二环氧乙烷的不对称环氧化;（2）了解机理， 手性二环氧乙烷不对称环氧化烯烃的影响因素; (3)确定酮催化剂所需的关键结构元素， 高不对称诱导和随后开发酮催化剂， 高稳定性、反应活性和对映选择性;（4）应用新的 发展了不对称环氧化合成生物活性 化合物和用于生物活性的手性结构单元 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.