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Metals in concert: Development of a new multi-component multi-catalysis domino reaction merging the Gold-mediated Meyer-Schuster Rearrangement with the Rh-catalyzed enantioselective conjugate addition of boronic acids

Metals in concert: Development of a new multi-component multi-catalysis domino reaction merging the Gold-mediated Meyer-Schuster Rearrangement with the Rh-catalyzed enantioselective conjugate addition of boronic acids
金属协同作用:开发一种新的多组分多催化多米诺骨牌反应,将金介导的迈耶-舒斯特重排与铑催化的硼酸对映选择性共轭加成相结合
批准号:
243775761
负责人:
Dr. Steffen Kreß
金额:
$0.0万
依托单位:
依托单位国家:
德国
项目类别:
Research Fellowships
财政年份:
2013
资助国家:
德国
项目状态:
已结题
起止时间:
2012-12-31 至 2014-12-31

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中文摘要
翻译
多米诺过程使资源和时间有效的过程在(不对称)有机合成中实现结构复杂性。这一领域的一种新兴的、基本上未被探索的方法是在一个反应容器中并行使用两种或两种以上的金属和相应的配体。这项工作的目的是开发一种方法,将原子经济的Au催化的简单且高度模块化的可及丙叉醇的重排与Rh催化的硼酸衍生物的1,4-对映选择性加成相结合。通过这种一锅策略,通过避免生成的中间体的纯化步骤,大大减少了合成β-手性羰基化合物的时间和材料成本。通过配体系统的变化,将确定相互兼容的催化剂,其选择性将相对于所需的多米诺骨牌过程进行检查。这种方法的潜力将通过改变取代基的空间和电子性质来探索。这种方法的发展使得能够高度灵活地制备用于天然产品和药物合成的高度灵活的对映体纯构建块。
英文摘要
Domino processes enable resource- and time-effective processes for the realization of structural complexity in (asymmetric) organic synthesis. An emerging and largely unexplored approach in this area is the parallel use of two or more metals and corresponding ligands in one reaction vessel. The aim of this work is the development of a method merging the atom-economic Au-catalyzed rearrangement of simple and highly modular accessible propargylic alcohols with the Rh-catalyzed enantioselective 1,4-Addition of boronic acid derivatives. By this one-pot strategy, the time efforts and the material costs regarding the synthesis of beta-chiral carbonyl compounds will be reduced drastically by avoiding purification steps of the generated intermediates. By variation of the ligand systems mutually compatible catalysts will be determined whose selectivities are examined with respect to the desired domino process. The potential of this method will be probed by varying the steric and electronic properties of the substituents. The development of such processes enables highly flexible preparation of enantiomerically pure building blocks for natural product and drug synthesis.
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