Synthesis of 3-fluoro-3-aryl oxindoles: Direct enantioselective α arylation of amides

Handle URI:
http://hdl.handle.net/10754/562087
Title:
Synthesis of 3-fluoro-3-aryl oxindoles: Direct enantioselective α arylation of amides
Authors:
Wu, Linglin; Falivene, Laura; Drinkel, Emma E.; Grant, Sharday; Linden, Anthony; Cavallo, Luigi ( 0000-0002-1398-338X ) ; Dorta, Reto
Abstract:
Modus operandi: Catalytic access to the title compounds through a new asymmetric α-arylation protocol is reported (see scheme). These products are formed in good yields and excellent enantioselectivities by using a new and easily synthesized chiral N-heterocyclic carbene (NHC) ligand. Advanced DFT calculations reveal the properties of the NHC ligand and the mode of operation of the catalyst. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division; KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program
Publisher:
Wiley-Blackwell
Journal:
Angewandte Chemie International Edition
Issue Date:
6-Feb-2012
DOI:
10.1002/anie.201200206
Type:
Article
ISSN:
14337851
Is Supplemented By:
Wu, L., Falivene, L., Drinkel, E., Grant, S., Linden, A., Cavallo, L., & Dorta, R. (2012). CCDC 861317: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccxx8fh; DOI:10.5517/ccxx8fh; HANDLE:http://hdl.handle.net/10754/624669; Wu, L., Falivene, L., Drinkel, E., Grant, S., Linden, A., Cavallo, L., & Dorta, R. (2012). CCDC 861318: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccxx8gj; DOI:10.5517/ccxx8gj; HANDLE:http://hdl.handle.net/10754/624670
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorWu, Linglinen
dc.contributor.authorFalivene, Lauraen
dc.contributor.authorDrinkel, Emma E.en
dc.contributor.authorGrant, Shardayen
dc.contributor.authorLinden, Anthonyen
dc.contributor.authorCavallo, Luigien
dc.contributor.authorDorta, Retoen
dc.date.accessioned2015-08-03T09:44:29Zen
dc.date.available2015-08-03T09:44:29Zen
dc.date.issued2012-02-06en
dc.identifier.issn14337851en
dc.identifier.doi10.1002/anie.201200206en
dc.identifier.urihttp://hdl.handle.net/10754/562087en
dc.description.abstractModus operandi: Catalytic access to the title compounds through a new asymmetric α-arylation protocol is reported (see scheme). These products are formed in good yields and excellent enantioselectivities by using a new and easily synthesized chiral N-heterocyclic carbene (NHC) ligand. Advanced DFT calculations reveal the properties of the NHC ligand and the mode of operation of the catalyst. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.en
dc.publisherWiley-Blackwellen
dc.subjectasymmetric catalysisen
dc.subjectN-heterocyclic carbenesen
dc.subjectoxindolesen
dc.subjectpalladiumen
dc.subjectsynthetic methodsen
dc.titleSynthesis of 3-fluoro-3-aryl oxindoles: Direct enantioselective α arylation of amidesen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.identifier.journalAngewandte Chemie International Editionen
dc.contributor.institutionOrganisch-Chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerlanden
dc.contributor.institutionDipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, 84084 Fisciano, Italyen
dc.contributor.institutionSchool of Chemistry and Biochemistry, University of Western Australia, 35 Stirling Highway, Crawley, WA 6009, Australiaen
kaust.authorCavallo, Luigien
dc.relation.isSupplementedByWu, L., Falivene, L., Drinkel, E., Grant, S., Linden, A., Cavallo, L., & Dorta, R. (2012). CCDC 861317: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccxx8fhen
dc.relation.isSupplementedByDOI:10.5517/ccxx8fhen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624669en
dc.relation.isSupplementedByWu, L., Falivene, L., Drinkel, E., Grant, S., Linden, A., Cavallo, L., & Dorta, R. (2012). CCDC 861318: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccxx8gjen
dc.relation.isSupplementedByDOI:10.5517/ccxx8gjen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624670en
All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.