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  Synthetic and mechanistic studies in enantioselective allylic substitutions catalysed by palladium complexes of a modular class of axially chiral quinazoline-containing ligands

Carroll, A.-M., McCarthy, M., Lacey, P. M., Saunders, C. P., Connolly, D. J., Farrell, A., et al. (2020). Synthetic and mechanistic studies in enantioselective allylic substitutions catalysed by palladium complexes of a modular class of axially chiral quinazoline-containing ligands. Tetrahedron, 76(1): 130780. doi:10.1016/j.tet.2019.130780.

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 Urheber:
Carroll, Anne-Marie1, Autor
McCarthy, Mary1, Autor
Lacey, Patrick M.1, Autor
Saunders, Cormac P.1, Autor
Connolly, David J.1, Autor
Farrell, Annette1, Autor
Rokade, Balaji V.1, 2, Autor
Goddard, Richard3, Autor           
Fristrup, Peter4, Autor
Norrby, Per-Ola5, Autor
Guiry, Patrick J.1, 2, Autor
Affiliations:
1Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland, ou_persistent22              
2Beacon Bioeconomy Centre, School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland, ou_persistent22              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              
4Isotope Chemistry, API Development, CMC, Research & Development, Novo Nordisk A/S, Denmark, ou_persistent22              
5Department of Chemistry and Molecular Biology, University of Gothenburg, Sweden, ou_persistent22              

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Schlagwörter: Asymmetric catalysis; Allylic alkylation; P,N ligands; Palladium; NMR; Computational studies
 Zusammenfassung: The application of palladium complexes of a modular series of axially chiral phosphinamine ligands, the Quinazolinaps, to the enantioselective alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate and methyl dimethyl malonate is described. Complete conversions and enantiomeric excesses of up to 91% were obtained. To elucidate the solution structure of these complexes and their dynamic behaviour, 2D COSY and NOESY NMR experiments were carried out. An X-ray crystal structure of a palladacycle derived from 2-phenylQuinazolinap which possesses two Pd3Cl5 units is shown. Computational studies were also undertaken to allow qualitative predictions of diastereomeric ratios. The observed enantioselectivity was then rationalised in terms of combined spectroscopic and theoretical data. The catalytic results obtained are best interpreted by the reaction proceeding with nucleophilic attack on the allyl trans to the phosphorus donor atom of the major diastereomeric intermediate.

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Sprache(n): eng - English
 Datum: 2019-09-242019-11-072019-11-182020-01-03
 Publikationsstatus: Erschienen
 Seiten: 19
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: DOI: 10.1016/j.tet.2019.130780
 Art des Abschluß: -

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Titel: Tetrahedron
  Andere : Tetrahedron
Genre der Quelle: Zeitschrift
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Ort, Verlag, Ausgabe: Kidlington : Elsevier Science
Seiten: - Band / Heft: 76 (1) Artikelnummer: 130780 Start- / Endseite: - Identifikator: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/00404020