Tandem Organocatalysis: Chlorination-Michael-Aldol Reaction

描述(由申请人提供)： 将简单的非手性分子转化为立体化学复杂的分子仍然是有机合成中的一个核心挑战。不对称金属催化为迎接这一挑战提供了一条途径。然而，大多数不对称有机金属催化剂只催化一种类型的反应，并允许一种转化。因此，传统上复杂的有机分子往往是通过转化来构建的。这一过程既繁琐又昂贵。这项提议描述了一种不对称催化的创新方法，不对称串联有机催化，它使用一个催化剂来调节多个转化。串联有机催化的应用将在一种潜在的极具药用价值的分子EiseniaclA的非常简明的合成中得到证明。这项研究的完成将表明串联有机催化的概念是有效的，并且优于传统的一种催化剂-一转化有机金属催化。更重要的是，不对称串联有机催化的实现将提供大量以其他方式无法获得的潜在候选药物。

DESCRIPTION (provided by applicant): Transforming simple achiral molecules into stereochemically complex molecules remains a central challenge in organic synthesis. Asymmetric metal catalysis provides an avenue to meet this challenge. However, the majority of asymmetric organometallic catalysts mediates one type of reaction and allows one transformation. Therefore, traditionally complex organic molecules are often built transformation by transformation. This process is tedious and expensive. This proposal describes an innovative approach to asymmetric catalysis, asymmetric tandem organocatalysis, which uses one catalyst to mediate multiple transformations. The utility of tandem organocatalysis will be demonstrated in a very concise synthesis of Eiseniachloride A, a molecule of potential great medicinal interest. The completion of this proposed research would show the concept of tandem organocatalysis is valid and superior to the traditional one catalyst-one transformation organometallic catalysis. More importantly, the realization of asymmetric tandem organocatalysis would provide large quantities of potential drug candidates that can not be obtained otherwise.