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Asymmetric Friedel-Crafts alkylation of electron-rich N-heterocycles with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline) and bis(thiazoline) Zn(II) complexes.
Chem Asian J. 2008 Jul 07; 3(7):1111-21.CA

Abstract

The asymmetric Friedel-Crafts alkylation of electron-rich N-containing heterocycles with nitroalkenes under catalysis of diphenylamine-tethered bis(oxazoline) and bis(thiazoline)-Zn(II) complexes was investigated. In the reaction of indole derivatives, the complex of ligand 4 f with trans-diphenyl substitutions afforded better results than previously published ligand 4 e with cis-diphenyl substitutions. Excellent yields (up to greater than 99 %) and enantioselectivities (up to 97 %) were achieved in most cases. The complex of ligand 4 d bearing tert-butyl groups gave the best results in the reactions of pyrrole. Moderate to good yields (up to 91 %) and enantioselectivities (up to 91 %) were achieved in most cases. The origin of the enantioselectivity was attributed to the NH-pi interaction between the catalyst and the incoming aromatic system in the transition state. Such an interaction was confirmed through comparison of the enantioselectivity and the absolute configuration of the products in the reactions catalyzed by designed ligands.

Authors+Show Affiliations

Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

18494013

Citation

Liu, Han, et al. "Asymmetric Friedel-Crafts Alkylation of Electron-rich N-heterocycles With Nitroalkenes Catalyzed By Diphenylamine-tethered Bis(oxazoline) and Bis(thiazoline) Zn(II) Complexes." Chemistry, an Asian Journal, vol. 3, no. 7, 2008, pp. 1111-21.
Liu H, Lu SF, Xu J, et al. Asymmetric Friedel-Crafts alkylation of electron-rich N-heterocycles with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline) and bis(thiazoline) Zn(II) complexes. Chem Asian J. 2008;3(7):1111-21.
Liu, H., Lu, S. F., Xu, J., & Du, D. M. (2008). Asymmetric Friedel-Crafts alkylation of electron-rich N-heterocycles with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline) and bis(thiazoline) Zn(II) complexes. Chemistry, an Asian Journal, 3(7), 1111-21. https://doi.org/10.1002/asia.200800071
Liu H, et al. Asymmetric Friedel-Crafts Alkylation of Electron-rich N-heterocycles With Nitroalkenes Catalyzed By Diphenylamine-tethered Bis(oxazoline) and Bis(thiazoline) Zn(II) Complexes. Chem Asian J. 2008 Jul 7;3(7):1111-21. PubMed PMID: 18494013.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric Friedel-Crafts alkylation of electron-rich N-heterocycles with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline) and bis(thiazoline) Zn(II) complexes. AU - Liu,Han, AU - Lu,Shao-Feng, AU - Xu,Jiaxi, AU - Du,Da-Ming, PY - 2008/5/22/pubmed PY - 2008/8/14/medline PY - 2008/5/22/entrez SP - 1111 EP - 21 JF - Chemistry, an Asian journal JO - Chem Asian J VL - 3 IS - 7 N2 - The asymmetric Friedel-Crafts alkylation of electron-rich N-containing heterocycles with nitroalkenes under catalysis of diphenylamine-tethered bis(oxazoline) and bis(thiazoline)-Zn(II) complexes was investigated. In the reaction of indole derivatives, the complex of ligand 4 f with trans-diphenyl substitutions afforded better results than previously published ligand 4 e with cis-diphenyl substitutions. Excellent yields (up to greater than 99 %) and enantioselectivities (up to 97 %) were achieved in most cases. The complex of ligand 4 d bearing tert-butyl groups gave the best results in the reactions of pyrrole. Moderate to good yields (up to 91 %) and enantioselectivities (up to 91 %) were achieved in most cases. The origin of the enantioselectivity was attributed to the NH-pi interaction between the catalyst and the incoming aromatic system in the transition state. Such an interaction was confirmed through comparison of the enantioselectivity and the absolute configuration of the products in the reactions catalyzed by designed ligands. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/18494013/Asymmetric_Friedel_Crafts_alkylation_of_electron_rich_N_heterocycles_with_nitroalkenes_catalyzed_by_diphenylamine_tethered_bis_oxazoline__and_bis_thiazoline__Zn_II__complexes_ L2 - https://doi.org/10.1002/asia.200800071 DB - PRIME DP - Unbound Medicine ER -