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首页> 外文期刊>Chemistry: A European journal >Designing 'Totem' C-2-Symmetrical Iron Porphyrin Catalysts for Stereoselective Cyclopropanations
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Designing 'Totem' C-2-Symmetrical Iron Porphyrin Catalysts for Stereoselective Cyclopropanations

机译：设计用于立体选择性环丙烷的“图腾” C-2-对称铁卟啉催化剂

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摘要

The catalytic activity of the iron(III) C-2 chiral porphyrin Fe(2)(OMe) in alkene cyclopropanation is herein reported. The catalyst promoted the reaction of differently substituted styrenes with diazo derivatives with trans-diastereoselectivities and enantioselectivities up to 99: 1 and 87 %, respectively. In addition, high TON and TOF values (up to 10000 and 120 000 h(-1), respectively) were observed indicating good activity and stability of the catalyst in optimized experimental conditions. The study of the cyclopropanation reaction revealed that the porphyrin skeleton is composed of two 'totem' parts which were independently responsible for the observed enantio-and diastereoselectivities. To further our research we also investigated the catalytic role of the methoxy axial ligand coordinated to the iron atom. The molecular structure of Fe(2)(OMe) was optimized by DFT calculations which were also employed to achieve a better understanding of the mechanistic details of the carbene transfer reaction.
机译：本文报道了铁（III）C-2手性卟啉Fe（2）（OMe）在烯烃环丙烷化中的催化活性。该催化剂促进了不同取代的苯乙烯与重氮非对映选择性和对映选择性分别高达99：1和87％的重氮衍生物的反应。此外，观察到较高的TON和TOF值（分别高达10000和120 000 h（-1）），表明在优化的实验条件下催化剂具有良好的活性和稳定性。对环丙烷化反应的研究表明，卟啉骨架由两个“图腾”部分组成，这两个部分分别负责观察到的对映异构和非对映异构选择性。为了进一步研究，我们还研究了与铁原子配位的甲氧基轴向配体的催化作用。 Fe（2）（OMe）的分子结构通过DFT计算进行了优化，该计算还用于更好地理解卡宾转移反应的机理细节。

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