Department of Chemistry and Pharmacy, Institute of Organic Chemistry I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander University Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058 Erlangen, Germany.
Department of Chemistry, Centro de Investigación y de Estudios Avanzados, Av. Instituto Politécnico Nacional 2508, 07360 Ciudad de México, Mexico.
Molecules. 2019 Sep 1;24(17):3182. doi: 10.3390/molecules24173182.
Catalysis mediated by iron complexes is emerging as an eco-friendly and inexpensive option in comparison to traditional metal catalysis. The epoxidation of alkenes constitutes an attractive application of iron(III) catalysis, in which terminal olefins are challenging substrates. Herein, we describe our study on the design of biomimetic non-heme ligands for the in situ generation of iron(III) complexes and their evaluation as potential catalysts in epoxidation of terminal olefins. Since it is well-known that active sites of oxidases might involve imidazole fragment of histidine, various simple imidazole derivatives (seven compounds) were initially evaluated in order to find the best reaction conditions and to develop, subsequently, more elaborated amino acid-derived peptide-like chiral ligands (10 derivatives) for enantioselective epoxidations.
与传统金属催化相比，铁配合物介导的催化作为一种环保且廉价的选择正在兴起。烯烃的环氧化反应是铁(III)催化的一种很有吸引力的应用，其中末端烯烃是具有挑战性的底物。在此，我们描述了我们设计仿生非血红素配体用于原位生成铁(III)配合物及其作为末端烯烃环氧化潜在催化剂的研究。由于众所周知，氧化酶的活性位点可能涉及组氨酸的咪唑片段，因此最初评估了各种简单的咪唑衍生物（七种化合物），以找到最佳反应条件，并随后开发出更复杂的衍生自氨基酸的肽类手性配体（十种衍生物）用于对映选择性环氧化反应。
