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- W3060712741 abstract "To gain insights into 2-indolylmethanol-involved reactions and to understand the origins of regioselectivity and enantioselectivity, theoretical investigations on the reaction mechanisms of three representative cycloadditions of 2-indolylmethanols have been carried out. In Ir-catalyzed regioselective (3 + 3) cycloaddition, it was found that the great difference between the energy barriers of the first initiating steps of the two pathways played a key role in determining the observed high regioselectivity and the C3-nucleophilicity of 2-indolylmethanol in this reaction. In chiral phosphoric acid (CPA)-catalyzed regioselective and enantioselective (3 + 3) and (3 + 4) cycloadditions, it was discovered that the great difference between the energy barriers of the transition states corresponding to the (R)- and (S)-configurations led to the observed high enantioselectivity of the products. In the presence of CPA, the C3-nucleophilicity of 2-indolylmethanol increased, resulting in exclusive regioselectivity. It was discovered that the electronic nature is not a decisive factor for the observed C3-regioselectivity in the delocalized cation of 2-indolylmethanol, and the steric factor should play a crucial role in the observed C3-regioselectivity. This study offers insights into the mechanisms of 2-indolylmethanol-involved reactions, which will give an in-depth understanding of the chemistry of 2-indolylmethanols and advance the development of this research field." @default.
- W3060712741 created "2020-08-24" @default.
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- W3060712741 date "2020-08-19" @default.
- W3060712741 modified "2023-10-15" @default.
- W3060712741 title "Insights into 2-Indolylmethanol-Involved Cycloadditions: Origins of Regioselectivity and Enantioselectivity" @default.
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- W3060712741 doi "https://doi.org/10.1021/acs.joc.0c01123" @default.
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