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- Publisher Website: 10.1002/asia.200800071
- Scopus: eid_2-s2.0-49149128980
- PMID: 18494013
- WOS: WOS:000257621100004
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Article: Asymmetric Friedel-Crafts alkylation of electron-rich N-heterocycles with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline) and bis(thiazoline) ZnII complexes
Title | Asymmetric Friedel-Crafts alkylation of electron-rich N-heterocycles with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline) and bis(thiazoline) Zn<sup>II</sup> complexes |
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Authors | |
Keywords | Pyrroles Friedel-Crafts reaction Asymmetric catalysis Nitroalkenes Indoles |
Issue Date | 2008 |
Citation | Chemistry - An Asian Journal, 2008, v. 3, n. 7, p. 1111-1121 How to Cite? |
Abstract | The asymmetric Friedel-Crafts alkylation of electron-rich N-containing heterocycles with nitroalkenes under catalysis of diphenylamine-tethered bis(oxazoline) and bis(thiazoline)-ZnII 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 4e 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 4d 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-π 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. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA. |
Persistent Identifier | http://hdl.handle.net/10722/291847 |
ISSN | 2023 Impact Factor: 3.5 2023 SCImago Journal Rankings: 0.846 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Liu, Han | - |
dc.contributor.author | Lu, Shao Feng | - |
dc.contributor.author | Xu, Jiaxi | - |
dc.contributor.author | Du, Da Ming | - |
dc.date.accessioned | 2020-11-17T14:55:14Z | - |
dc.date.available | 2020-11-17T14:55:14Z | - |
dc.date.issued | 2008 | - |
dc.identifier.citation | Chemistry - An Asian Journal, 2008, v. 3, n. 7, p. 1111-1121 | - |
dc.identifier.issn | 1861-4728 | - |
dc.identifier.uri | http://hdl.handle.net/10722/291847 | - |
dc.description.abstract | The asymmetric Friedel-Crafts alkylation of electron-rich N-containing heterocycles with nitroalkenes under catalysis of diphenylamine-tethered bis(oxazoline) and bis(thiazoline)-ZnII 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 4e 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 4d 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-π 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. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA. | - |
dc.language | eng | - |
dc.relation.ispartof | Chemistry - An Asian Journal | - |
dc.subject | Pyrroles | - |
dc.subject | Friedel-Crafts reaction | - |
dc.subject | Asymmetric catalysis | - |
dc.subject | Nitroalkenes | - |
dc.subject | Indoles | - |
dc.title | Asymmetric Friedel-Crafts alkylation of electron-rich N-heterocycles with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline) and bis(thiazoline) Zn<sup>II</sup> complexes | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/asia.200800071 | - |
dc.identifier.pmid | 18494013 | - |
dc.identifier.scopus | eid_2-s2.0-49149128980 | - |
dc.identifier.volume | 3 | - |
dc.identifier.issue | 7 | - |
dc.identifier.spage | 1111 | - |
dc.identifier.epage | 1121 | - |
dc.identifier.eissn | 1861-471X | - |
dc.identifier.isi | WOS:000257621100004 | - |
dc.identifier.issnl | 1861-471X | - |