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    Home > Xu Senmiao team of Lanzhou Institute of chemistry, Chinese Academy of Sciences has made new progress in asymmetric hydrocarbon bond boration of cyclopropane

    Xu Senmiao team of Lanzhou Institute of chemistry, Chinese Academy of Sciences has made new progress in asymmetric hydrocarbon bond boration of cyclopropane

    • Last Update: 2019-07-13
    • Source: Internet
    • Author: User
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    Optically active cyclopropanes are widely found in natural products and have important application value in organic synthesis, pharmaceutical chemistry and catalytic materials Among them, cyclopropanic boric acid has attracted more and more attention because it can utilize the stereospecific reaction of C-B bond to realize the diversity of products At present, most of the synthesis methods of these compounds need to pre activate the substrate, which leads to additional operation steps and more consumption of reagents and solvents Therefore, the development steps and the catalytic asymmetric method of atomic economy will play an important role in promoting the development of this field Xu Senmiao, State Key Laboratory of carbonylation and selective oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, has been committed to the study of transition metal catalyzed regionally and stereoselective boration (org Lett 2017, 19, 3676; chem SCI 2018, 9, 5855; J am Chem SOC 2019, 141, 5334; angel Chem Int ed 2019, 58, 8187) Especially in the aspect of asymmetric hydrocarbon bond boration, they have developed a new type of chiral bidentate boron ligands and realized the asymmetric boration of C (SP 2) - H bond of diarylmethylamine (J am Chem SOC 2019, 141, 5334) for the first time Recently, they have realized the asymmetric boration of C (SP 3) - H bond of cyclopropanes catalyzed by transition metal iridium for the first time by using the improved chiral bidentate boron ligands Using cyclopropylformamide as the substrate, they realized the asymmetric C (SP 3) - H bond boration reaction catalyzed by iridium using the chiral boron ligand L the highest EE value of the product can reach 96%, and it has a very wide spectrum of functional group compatibility The absolute configuration of the product was determined by single crystal At the same time, this method can also be applied to the later modification of some bioactive molecules with cyclopropane Fig 1 Application of the product (source: J am Chem SOC.) the researchers have also studied the conversion of carbon and boron bond of the product, synthesized the drug molecular l-minapram for the treatment of antidepressant, proposed the possible reaction mechanism, and explained the control factor of enantioselectivity Fig 2 possible reaction mechanism (source: J am Chem SOC.) related results are published online in J am Chem SOC (DOI: 10.1021 / JACS 9b04549) The above work has been supported by NSFC, NSFC of Jiangsu Province, Lanzhou Institute of Chemical Sciences, State Key Laboratory of carbonyl synthesis and selective oxidation, and Key Laboratory of organosilicon chemistry and materials technology, Ministry of education, Hangzhou Normal University.
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