Enantioselective Functionalizations of alpha-, beta-Unsaturated Carboxylic Acids using Chiral Boronic Acids

使用手性硼酸对 α-、β-不饱和羧酸进行对映选择性官能化

• 批准号: 436477447
• 负责人: Dr. Moritz Balkenhohl
• 金额: --
• 依托单位: Laboratorium für Organische Chemie
• 依托单位国家: 德国
• 项目类别: Research Fellowships
• 财政年份: 2019
• 资助国家: 德国
• 起止时间: 2018-12-31 至 2020-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/436477447?language=en
• 关键词: Enantioselective; Functionalizations; alpha; beta; Unsaturated

The enantioselective functionalization of olefins plays a highly important role in modern organic synthesis. So far, a wide variety of asymmetric alkene functionalizations have been reported, with new publications appearing weekly on this very active research field. However, the use of α,β-unsaturated carboxylic acids in alkene transformations remains rather undisclosed and only selected reactions, such as hydrogenations or cycloadditions, are known.Herein it is proposed, that the use of a chiral boronic acid may pave the way for the enantioselective functionalization of α,β-unsaturated carboxylic acids. The carboxylic acid together with the boronic acid should form a boronate intermediate, which may be susceptible towards several transformations, which would allow the asymmetric preparation of a wide range of functionalized carboxylic acids. The project will close the gap in the current state of olefin functionalization and lead to the development of methodologies towards the preparation of chiral carboxylic acids, which are present in a large number of pharmaceuticals and natural products.

烯烃的不对称功能化在现代有机合成中起着非常重要的作用。到目前为止，已经报道了各种各样的不对称烯烃官能化，每周都有新的出版物出现在这个非常活跃的研究领域。然而，α，β-不饱和羧酸在烯烃转化中的使用仍然相当未公开，并且仅已知选定的反应，例如氢化或环加成。羧酸与硼酸一起应形成硼酸酯中间体，其可易于发生几种转化，这将允许不对称制备宽范围的官能化羧酸。该项目将缩小目前烯烃官能化方面的差距，并导致开发制备手性羧酸的方法，手性羧酸存在于大量药物和天然产物中。