About: Chiral phosphinoferrocene carboxamides with amino acid substituents as ligands for Pd-catalysed asymmetric allylic substitutions. Synthesis and structural characterisation of catalytically relevant Pd complexes     Goto   Sponge   NotDistinct   Permalink

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Description
  • An extensive series of chiral amino acid amides prepared from 1'-(diphenylphosphino)ferrocene-1-carboxylic acid (Hdpf) or its planar-chiral isomer, 2-(diphenylphosphino)ferrocene-1-carboxylic acid, have been tested as ligands for Pd-catalysed asymmetric allylic substitution reactions. In alkylation of 1,3-diphenylallyl acetate as a model substrate with dimethyl malonate the ligands performed well in terms of both reaction rate and enantioselectivity, achieving up to 98% ee. In contrast, the reactions of the same substrate with other nucleophiles proceeded either slowly and with poor ee's (amination with benzylamine) or not at all (etherification with benzyl alcohol). In order to rationalise the influence of the ligand structure on the reaction course, three model complexes, viz. [(h3-methallyl)PdCl(L-kP)], [(h3-methallyl)Pd(L-k2O,P)]ClO4 and [(h3-methallyl)Pd(L-kP)2]ClO4 have been prepared from the achiral amide Ph2PfcCONHCH2CO2Me (L; fc = ferrocene-1,1'-diyl) and structurally characterised.
  • An extensive series of chiral amino acid amides prepared from 1'-(diphenylphosphino)ferrocene-1-carboxylic acid (Hdpf) or its planar-chiral isomer, 2-(diphenylphosphino)ferrocene-1-carboxylic acid, have been tested as ligands for Pd-catalysed asymmetric allylic substitution reactions. In alkylation of 1,3-diphenylallyl acetate as a model substrate with dimethyl malonate the ligands performed well in terms of both reaction rate and enantioselectivity, achieving up to 98% ee. In contrast, the reactions of the same substrate with other nucleophiles proceeded either slowly and with poor ee's (amination with benzylamine) or not at all (etherification with benzyl alcohol). In order to rationalise the influence of the ligand structure on the reaction course, three model complexes, viz. [(h3-methallyl)PdCl(L-kP)], [(h3-methallyl)Pd(L-k2O,P)]ClO4 and [(h3-methallyl)Pd(L-kP)2]ClO4 have been prepared from the achiral amide Ph2PfcCONHCH2CO2Me (L; fc = ferrocene-1,1'-diyl) and structurally characterised. (en)
Title
  • Chiral phosphinoferrocene carboxamides with amino acid substituents as ligands for Pd-catalysed asymmetric allylic substitutions. Synthesis and structural characterisation of catalytically relevant Pd complexes
  • Chiral phosphinoferrocene carboxamides with amino acid substituents as ligands for Pd-catalysed asymmetric allylic substitutions. Synthesis and structural characterisation of catalytically relevant Pd complexes (en)
skos:prefLabel
  • Chiral phosphinoferrocene carboxamides with amino acid substituents as ligands for Pd-catalysed asymmetric allylic substitutions. Synthesis and structural characterisation of catalytically relevant Pd complexes
  • Chiral phosphinoferrocene carboxamides with amino acid substituents as ligands for Pd-catalysed asymmetric allylic substitutions. Synthesis and structural characterisation of catalytically relevant Pd complexes (en)
skos:notation
  • RIV/00216208:11310/11:10101070!RIV12-MSM-11310___
http://linked.open...avai/predkladatel
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(LC06070), S, Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika
  • 44
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 190199
http://linked.open...ai/riv/idVysledku
  • RIV/00216208:11310/11:10101070
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • Coordination study; Palladium; Asymmetric allylic substitution; Amino acids; Amides; Phosphines; Ferrocene ligands (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV
  • [7F2C520F1C9F]
http://linked.open...i/riv/nazevZdroje
  • Dalton Transactions
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 40
http://linked.open...iv/tvurceVysledku
  • Císařová, Ivana
  • Tauchman, Jiří
  • Štěpnička, Petr
http://linked.open...ain/vavai/riv/wos
  • 000296776200014
http://linked.open...n/vavai/riv/zamer
issn
  • 1477-9226
number of pages
http://bibframe.org/vocab/doi
  • 10.1039/c1dt11230a
http://localhost/t...ganizacniJednotka
  • 11310
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