High pressure liquid chromatography for the analysis of enantiomerically enriched products

用于分析对映体富集产品的高压液相色谱

• 批准号: 345349-2007
• 负责人: Gravel, Michel
• 金额: $ 5.1万
• 依托单位: University of Saskatchewan
• 依托单位国家: 加拿大
• 项目类别: Research Tools and Instruments - Category 1 (<$150,000)
• 财政年份: 2006
• 资助国家: 加拿大
• 起止时间: 2006-01-01 至 2007-12-31
• 项目状态: 已结题
• 来源: https://www.nserc-crsng.gc.ca/ase-oro/Details-Detailles_eng.asp?id=325906
• 关键词: pressure; liquid; chromatography; analysis; enantiomerically

The equipment requested in this grant is a high-pressure liquid chromatography system with the capability of performing enantiomer separation. This instrument will be used to analyze the enantiomeric composition of chiral compounds prepared using organocatalytic methods.    Asymmetric catalysis using organic molecules (organocatalysis) has recently emerged as a powerful approach for the synthesis of organic compounds in an enantioselective fashion. Despite the great advances accomplished in this area, most methods developed so far show a narrow scope of reagents. Also, the catalysts reported thus far show very little variety in their scaffold and the nature of their catalysis. The purpose of this research is to develop new classes of organocatalysts and new catalytic modes of action that will complement and expand existing methodology. In order to achieve these goals, three different areas will be explored: asymmetric phase transfer catalysis, multifunctional catalysis, and Lewis base-catalyzed Diels-Alder reactions.    In the first part of the program, phase transfer catalysts possessing novel scaffolds will be synthesized in order to broaden the scope and to improve the stability of this type of catalysts. In the area of multifunctional catalysis, various types of activating groups, such as substituted guanidines, will be introduced. These groups will display increased reactivity as well as the ability to tune their activity through the judicious choice of their substituents. Finally, the application of Lewis base catalysts to the Diels-Alder reaction will dramatically expand the scope of available reactive partners for this very important reaction. In particular, it will allow the use of a wide variety of functionalized dienes that are incompatible with commonly used Lewis acid catalysts.    The underlying theme of this research program is the asymmetric synthesis of useful chemical building blocks using organic molecules as catalysts. In order to assess the efficiency of these catalytic processes, the use of chiral high-pressure liquid chromatography will be essential.

本资助申请的设备是一个具有对映体分离能力的高压液相色谱系统。该仪器将用于分析使用有机催化方法制备的手性化合物的对映体组成。 利用有机分子的不对称催化（有机催化）是近年来兴起的一种对映选择性合成有机化合物的有效方法。尽管在这一领域取得了很大的进步，但迄今为止开发的大多数方法都显示出试剂范围狭窄。此外，迄今为止报道的催化剂在其支架和其催化性质方面表现出非常少的变化。本研究的目的是开发新的有机催化剂和新的催化作用模式，以补充和扩展现有的方法。为了实现这些目标，将探索三个不同的领域：不对称相转移催化，多功能催化和刘易斯碱催化的Diels-Alder反应。 在计划的第一部分中，将合成具有新型支架的相转移催化剂，以拓宽这类催化剂的范围并提高其稳定性。在多功能催化领域，将介绍各种类型的活化基团，如取代胍。这些基团将显示出增加的反应性以及通过明智地选择其取代基来调节其活性的能力。最后，刘易斯碱催化剂在狄尔斯-阿尔德反应中的应用将极大地扩大这一非常重要的反应的可用反应性伙伴的范围。特别地，它将允许使用与常用的刘易斯酸催化剂不相容的多种官能化二烯。 该研究计划的基本主题是使用有机分子作为催化剂的有用化学构件的不对称合成。为了评估这些催化过程的效率，使用手性高压液相色谱将是必不可少的。