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Catalytic asymmetric Friedel-Crafts/protonation of nitroalkenes and N-heteroaromatics.
J Org Chem. 2011 Jul 01; 76(13):5450-6.JO

Abstract

The catalytic asymmetric Friedel-Crafts/protonation of indoles and pyrroles with α-substituted nitroalkenes to give the corresponding adducts in a highly anti-selective manner was achieved by an imidazoline-aminophenol (L2)-Cu complex. The anti-adducts could be successfully transformed to biochemically important α-substituted β-heteroarylalkylamines.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Arai T
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan. tarai@faculty.chiba-u.jp
Awata A
No affiliation info available
Wasai M
No affiliation info available
Yokoyama N
No affiliation info available
Masu H
No affiliation info available

MeSH

AlkenesAminesCatalysisCrystallography, X-RayHeterocyclic CompoundsHydrocarbons, AromaticModels, MolecularMolecular StructureNitro CompoundsProtonsStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21598998

Citation

Arai, Takayoshi, et al. "Catalytic Asymmetric Friedel-Crafts/protonation of Nitroalkenes and N-heteroaromatics." The Journal of Organic Chemistry, vol. 76, no. 13, 2011, pp. 5450-6.
Arai T, Awata A, Wasai M, et al. Catalytic asymmetric Friedel-Crafts/protonation of nitroalkenes and N-heteroaromatics. J Org Chem. 2011;76(13):5450-6.
Arai, T., Awata, A., Wasai, M., Yokoyama, N., & Masu, H. (2011). Catalytic asymmetric Friedel-Crafts/protonation of nitroalkenes and N-heteroaromatics. The Journal of Organic Chemistry, 76(13), 5450-6. https://doi.org/10.1021/jo200546a
Arai T, et al. Catalytic Asymmetric Friedel-Crafts/protonation of Nitroalkenes and N-heteroaromatics. J Org Chem. 2011 Jul 1;76(13):5450-6. PubMed PMID: 21598998.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic asymmetric Friedel-Crafts/protonation of nitroalkenes and N-heteroaromatics. AU - Arai,Takayoshi, AU - Awata,Atsuko, AU - Wasai,Makiko, AU - Yokoyama,Naota, AU - Masu,Hyuma, Y1 - 2011/06/06/ PY - 2011/5/24/entrez PY - 2011/5/24/pubmed PY - 2011/10/25/medline SP - 5450 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 13 N2 - The catalytic asymmetric Friedel-Crafts/protonation of indoles and pyrroles with α-substituted nitroalkenes to give the corresponding adducts in a highly anti-selective manner was achieved by an imidazoline-aminophenol (L2)-Cu complex. The anti-adducts could be successfully transformed to biochemically important α-substituted β-heteroarylalkylamines. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21598998/Catalytic_asymmetric_Friedel_Crafts/protonation_of_nitroalkenes_and_N_heteroaromatics_ L2 - https://doi.org/10.1021/jo200546a DB - PRIME DP - Unbound Medicine ER -