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Statements

Subject Item
n2:RIV%2F00216208%3A11310%2F11%3A10101070%21RIV12-MSM-11310___
rdf:type
n9:Vysledek skos:Concept
rdfs:seeAlso
http://dx.doi.org/10.1039/c1dt11230a
dcterms: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.
dcterms: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
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
skos:notation
RIV/00216208:11310/11:10101070!RIV12-MSM-11310___
n9:predkladatel
n10:orjk%3A11310
n3:aktivita
n7:Z n7:S n7:P
n3:aktivity
P(LC06070), S, Z(MSM0021620857)
n3:cisloPeriodika
44
n3:dodaniDat
n18:2012
n3:domaciTvurceVysledku
n15:3157962 n15:8116997 n15:6298486
n3:druhVysledku
n11:J
n3:duvernostUdaju
n20:S
n3:entitaPredkladatele
n17:predkladatel
n3:idSjednocenehoVysledku
190199
n3:idVysledku
RIV/00216208:11310/11:10101070
n3:jazykVysledku
n14:eng
n3:klicovaSlova
Coordination study; Palladium; Asymmetric allylic substitution; Amino acids; Amides; Phosphines; Ferrocene ligands
n3:klicoveSlovo
n4:Asymmetric%20allylic%20substitution n4:Phosphines n4:Palladium n4:Amides n4:Coordination%20study n4:Amino%20acids n4:Ferrocene%20ligands
n3:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n3:kontrolniKodProRIV
[7F2C520F1C9F]
n3:nazevZdroje
Dalton Transactions
n3:obor
n22:CA
n3:pocetDomacichTvurcuVysledku
3
n3:pocetTvurcuVysledku
3
n3:projekt
n13:LC06070
n3:rokUplatneniVysledku
n18:2011
n3:svazekPeriodika
40
n3:tvurceVysledku
Císařová, Ivana Štěpnička, Petr Tauchman, Jiří
n3:wos
000296776200014
n3:zamer
n5:MSM0021620857
s:issn
1477-9226
s:numberOfPages
10
n21:doi
10.1039/c1dt11230a
n19:organizacniJednotka
11310