Chemical Sciences Division, Lawrence Berkeley National Laboratory and Department of Chemistry , University of California , Berkeley , California 94720 , United States.
J Am Chem Soc. 2020 Jan 15;142(2):733-737. doi: 10.1021/jacs.9b13177. Epub 2020 Jan 7.
It has been previously demonstrated that nanovessels can be highly competent catalysts providing high rate accelerations and unique selectivity to the organic transformations which they mediate. However, for supramolecular assemblies to be considered a standard reagent in organic synthesis they must first demonstrate the ability to catalyze increasingly complex transformations. Herein, we report a three-component Aza-Darzens reaction that generates -phenylaziridines, catalyzed by a supramolecular host, that provides the stereoisomer opposite to the one generated in bulk solution ( vs ). This transformation constitutes a rare catalytic three-component coupling within a supramolecular assembly, providing a supramolecular solution to a synthetically challenging transformation.
先前已经证明,纳米容器可以作为高效的催化剂,对它们介导的有机转化提供高反应速率和独特的选择性。然而,为了使超分子组装体被认为是有机合成中的标准试剂,它们必须首先证明能够催化越来越复杂的转化。在此,我们报告了一个三组分 Aza-Darzens 反应,该反应在超分子主体的催化下生成 -苯基氮丙啶,其立体异构体与在本体溶液中生成的相反( vs )。这种转化构成了超分子组装体中罕见的催化三组分偶联,为具有挑战性的合成转化提供了超分子解决方案。