ASYMMETRIC EPOXIDATION OF OLEFINS BY CHIRAL DIOXIRANES

手性二氧杂环己烷对烯烃的不对称环氧化

• 批准号: 2024256
• 负责人: YIAN SHI
• 金额: $ 8.59万
• 依托单位: COLORADO STATE UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 1997
• 资助国家: 美国
• 起止时间: 1997-05-01 至 2002-04-30
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/2024256
• 关键词: alkenes; chemical synthesis; epoxides; ethylene oxide; ketones; stereochemistry

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.

描述：拟议研究的总体目标是开发新的、 手性二环氧乙烷对烯烃进行高效催化不对称环氧化 由 Oxone（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，以及 低毒。 这些标准中的每一个对于适用性都非常重要 该方法用于合成生物活性化合物。 本研究的具体目标是：（1）综合各种 来自容易获得的手性起始材料的手性酮，例如 碳水化合物并测试这些手性酮的可行性 通过二氧杂环丙烷进行不对称环氧化； (2)了解其机理 手性二环氧乙烷对烯烃进行不对称环氧化的影响因素； (3)确定酮催化剂所需的关键结构元素 高不对称诱导，随后开发出酮催化剂 高稳定性、反应活性和对映选择性； (4) 申请新的 开发了不对称环氧化来合成生物活性物质 化合物和有用的具有生物活性的手性构件 化合物。