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Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters.
J Am Chem Soc. 2020 Jul 15; 142(28):11999-12004.JA

Abstract

We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.

Authors+Show Affiliations

Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Korea. Center for Catalytic Hydrocarbon Functionalization, Institute for Basic Science (IBS), Daejeon 34141, Korea.Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Korea. Center for Catalytic Hydrocarbon Functionalization, Institute for Basic Science (IBS), Daejeon 34141, Korea.Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Korea. Center for Catalytic Hydrocarbon Functionalization, Institute for Basic Science (IBS), Daejeon 34141, Korea.Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Korea. Center for Catalytic Hydrocarbon Functionalization, Institute for Basic Science (IBS), Daejeon 34141, Korea.Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Korea. Center for Catalytic Hydrocarbon Functionalization, Institute for Basic Science (IBS), Daejeon 34141, Korea.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32605371

Citation

Lee, Minhan, et al. "Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters." Journal of the American Chemical Society, vol. 142, no. 28, 2020, pp. 11999-12004.
Lee M, Jung H, Kim D, et al. Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters. J Am Chem Soc. 2020;142(28):11999-12004.
Lee, M., Jung, H., Kim, D., Park, J. W., & Chang, S. (2020). Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters. Journal of the American Chemical Society, 142(28), 11999-12004. https://doi.org/10.1021/jacs.0c04344
Lee M, et al. Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters. J Am Chem Soc. 2020 Jul 15;142(28):11999-12004. PubMed PMID: 32605371.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters. AU - Lee,Minhan, AU - Jung,Hoimin, AU - Kim,Dongwook, AU - Park,Jung-Woo, AU - Chang,Sukbok, Y1 - 2020/07/03/ PY - 2020/7/2/pubmed PY - 2020/7/2/medline PY - 2020/7/2/entrez SP - 11999 EP - 12004 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 142 IS - 28 N2 - We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/32605371/Modular_Tuning_of_Electrophilic_Reactivity_of_Iridium_Nitrenoids_for_the_Intermolecular_Selective_α-Amidation_of_β-Keto_Esters L2 - https://doi.org/10.1021/jacs.0c04344 DB - PRIME DP - Unbound Medicine ER -
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