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Asymmetric Friedel-Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes.
Org Biomol Chem. 2012 Jun 28; 10(24):4739-46.OB

Abstract

An efficient diastereo- and enantioselective Friedel-Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes has been developed. This asymmetric Friedel-Crafts alkylation led to medicinally privileged indolyl(nitro)chromans in good yields with high enantioselectivities (up to 95% ee) and diastereoselectivities under mild reaction conditions.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Jia Y
School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China.
Yang W
No affiliation info available
Du DM
No affiliation info available

MeSH

AlkylationBenzopyransCatalysisDiphenylamineIndolesMolecular StructureNitro CompoundsOxazolesStereoisomerismThiazolesZinc Compounds

Pub Type(s)

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

Language

eng

PubMed ID

22588514

Citation

Jia, Yang, et al. "Asymmetric Friedel-Crafts Alkylation of Indoles With 3-nitro-2H-chromenes Catalyzed By Diphenylamine-linked Bis(oxazoline) and Bis(thiazoline) Zn(II) Complexes." Organic & Biomolecular Chemistry, vol. 10, no. 24, 2012, pp. 4739-46.
Jia Y, Yang W, Du DM. Asymmetric Friedel-Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes. Org Biomol Chem. 2012;10(24):4739-46.
Jia, Y., Yang, W., & Du, D. M. (2012). Asymmetric Friedel-Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes. Organic & Biomolecular Chemistry, 10(24), 4739-46. https://doi.org/10.1039/c2ob25360g
Jia Y, Yang W, Du DM. Asymmetric Friedel-Crafts Alkylation of Indoles With 3-nitro-2H-chromenes Catalyzed By Diphenylamine-linked Bis(oxazoline) and Bis(thiazoline) Zn(II) Complexes. Org Biomol Chem. 2012 Jun 28;10(24):4739-46. PubMed PMID: 22588514.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric Friedel-Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes. AU - Jia,Yang, AU - Yang,Wen, AU - Du,Da-Ming, Y1 - 2012/05/15/ PY - 2012/5/17/entrez PY - 2012/5/17/pubmed PY - 2012/9/18/medline SP - 4739 EP - 46 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 10 IS - 24 N2 - An efficient diastereo- and enantioselective Friedel-Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes has been developed. This asymmetric Friedel-Crafts alkylation led to medicinally privileged indolyl(nitro)chromans in good yields with high enantioselectivities (up to 95% ee) and diastereoselectivities under mild reaction conditions. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/22588514/Asymmetric_Friedel_Crafts_alkylation_of_indoles_with_3_nitro_2H_chromenes_catalyzed_by_diphenylamine_linked_bis_oxazoline__and_bis_thiazoline__Zn_II__complexes_ L2 - https://doi.org/10.1039/c2ob25360g DB - PRIME DP - Unbound Medicine ER -
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