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Asymmetric Friedel-Crafts alkylation of methoxyfuran with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline)-Zn(II) complexes.
Org Lett. 2007 Nov 08; 9(23):4725-8.OL

Abstract

The first catalytic asymmetric Friedel-Crafts reaction of 2-methoxyfuran with nitroalkenes was developed under the catalysis of diphenylamine-tethered bis(oxazoline)-Zn(OTf)2 complexes. The reaction conditions and ligands were optimized, and the scope of the reaction was tested by varying the nitroalkenes. For most of aromatic and heteroaromatic nitroalkenes, good yields and high enantioselectivities (86-96% ee) were obtained. The methoxyfuran group in the product can be transformed to carboxylic acid via oxidative fragmentation with full retention of the configuration.

Authors+Show Affiliations

Liu H
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, P.R. China.
Xu J
No affiliation info available
Du DM
No affiliation info available

MeSH

AlkenesAlkylationCatalysisDiphenylamineFuransLigandsMolecular StructureNitro CompoundsOxazoloneOxidation-ReductionSolventsStereoisomerismZinc Compounds

Pub Type(s)

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

Language

eng

PubMed ID

17924637

Citation

Liu, Han, et al. "Asymmetric Friedel-Crafts Alkylation of Methoxyfuran With Nitroalkenes Catalyzed By Diphenylamine-tethered bis(oxazoline)-Zn(II) Complexes." Organic Letters, vol. 9, no. 23, 2007, pp. 4725-8.
Liu H, Xu J, Du DM. Asymmetric Friedel-Crafts alkylation of methoxyfuran with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline)-Zn(II) complexes. Org Lett. 2007;9(23):4725-8.
Liu, H., Xu, J., & Du, D. M. (2007). Asymmetric Friedel-Crafts alkylation of methoxyfuran with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline)-Zn(II) complexes. Organic Letters, 9(23), 4725-8.
Liu H, Xu J, Du DM. Asymmetric Friedel-Crafts Alkylation of Methoxyfuran With Nitroalkenes Catalyzed By Diphenylamine-tethered bis(oxazoline)-Zn(II) Complexes. Org Lett. 2007 Nov 8;9(23):4725-8. PubMed PMID: 17924637.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric Friedel-Crafts alkylation of methoxyfuran with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline)-Zn(II) complexes. AU - Liu,Han, AU - Xu,Jiaxi, AU - Du,Da-Ming, Y1 - 2007/10/09/ PY - 2007/10/11/pubmed PY - 2007/12/12/medline PY - 2007/10/11/entrez SP - 4725 EP - 8 JF - Organic letters JO - Org Lett VL - 9 IS - 23 N2 - The first catalytic asymmetric Friedel-Crafts reaction of 2-methoxyfuran with nitroalkenes was developed under the catalysis of diphenylamine-tethered bis(oxazoline)-Zn(OTf)2 complexes. The reaction conditions and ligands were optimized, and the scope of the reaction was tested by varying the nitroalkenes. For most of aromatic and heteroaromatic nitroalkenes, good yields and high enantioselectivities (86-96% ee) were obtained. The methoxyfuran group in the product can be transformed to carboxylic acid via oxidative fragmentation with full retention of the configuration. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17924637/Asymmetric_Friedel_Crafts_alkylation_of_methoxyfuran_with_nitroalkenes_catalyzed_by_diphenylamine_tethered_bis_oxazoline__Zn_II__complexes_ L2 - https://doi.org/10.1021/ol702003x DB - PRIME DP - Unbound Medicine ER -