High pressure liquid chromatography for the analysis of enantiomerically enriched products

这笔赠款所要求的设备是一种能够进行对映体分离的高压液相色谱系统。该仪器将用于分析用有机催化方法制备的手性化合物的对映体组成。使用有机分子的不对称催化(有机催化)最近已成为以对映选择性方式合成有机化合物的一种强有力的方法。尽管在这一领域取得了很大的进展，但到目前为止开发的大多数方法显示试剂的范围很窄。此外，到目前为止报道的催化剂在其支架和催化性质上的变化很小。这项研究的目的是开发新的有机催化剂类别和新的催化作用模式，以补充和扩展现有的方法学。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Lewis碱催化的Diels-Alder反应。在该计划的第一部分，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，提高其稳定性。在多功能催化领域，将引入各种类型的活化基团，如取代鸟嘌呤类化合物。这些基团将表现出更强的反应性，以及通过明智地选择取代基来调整其活性的能力。最后，路易斯碱催化剂在Diels-Alder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伙伴的范围。特别是，它将允许使用与常用的Lewis酸催化剂不相容的各种官能化双烯。他说，这项研究计划的基本主题是使用有机分子作为催化剂不对称合成有用的化学构件。为了评估这些催化过程的效率，手性高压液相色谱的使用将是必不可少的。

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.