About: Synthesis, Molecular Structure, and Catalytic Evaluation of Centrostereogenic Ferrocenophane Phosphines

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About: Synthesis, Molecular Structure, and Catalytic Evaluation of Centrostereogenic Ferrocenophane Phosphines Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1021/om3011245
Description	1,1'-[(1R)-1-Diarylphosphino-1,3-propanediyl]ferrocenes, where aryl = phenyl, 2-tolyl, 4-tolyl, mesityl, 4-anisyl, 4-(trifluoromethyl)phenyl, were prepared as new chiral ferrocenophane phosphines featuring only central chirality in good yields by the reaction of the corresponding chiral alcohol, 1,1'-[(1R)-1-hydroxy-1,3-propanediyl]ferrocene, and diarylphosphines in the presence of chlorotrimethylsilane and sodium iodide. These phosphines were studied as ligands in palladium(II) complexes and further evaluated in two mechanistically different model catalytic reactions, namely in Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenylallyl acetate with dimethyl malonate, and in enantioselective aza-Morita-Baylis-Hillman reactions of aromatic N-sulfonyl imines with methyl vinyl ketone. 1,1'-[(1R)-1-Diarylphosphino-1,3-propanediyl]ferrocenes, where aryl = phenyl, 2-tolyl, 4-tolyl, mesityl, 4-anisyl, 4-(trifluoromethyl)phenyl, were prepared as new chiral ferrocenophane phosphines featuring only central chirality in good yields by the reaction of the corresponding chiral alcohol, 1,1'-[(1R)-1-hydroxy-1,3-propanediyl]ferrocene, and diarylphosphines in the presence of chlorotrimethylsilane and sodium iodide. These phosphines were studied as ligands in palladium(II) complexes and further evaluated in two mechanistically different model catalytic reactions, namely in Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenylallyl acetate with dimethyl malonate, and in enantioselective aza-Morita-Baylis-Hillman reactions of aromatic N-sulfonyl imines with methyl vinyl ketone. (en)
Title	Synthesis, Molecular Structure, and Catalytic Evaluation of Centrostereogenic Ferrocenophane Phosphines Synthesis, Molecular Structure, and Catalytic Evaluation of Centrostereogenic Ferrocenophane Phosphines (en)
skos:prefLabel	Synthesis, Molecular Structure, and Catalytic Evaluation of Centrostereogenic Ferrocenophane Phosphines Synthesis, Molecular Structure, and Catalytic Evaluation of Centrostereogenic Ferrocenophane Phosphines (en)
skos:notation	RIV/00216208:11310/13:10133858!RIV14-GA0-11310___
http://linked.open...avai/riv/aktivita	I P S Z
http://linked.open...avai/riv/aktivity	I, P(GAP207/10/0176), S, Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika	2
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Škoch, Karel Císařová, Ivana Štěpnička, Petr
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Karlova v Praze / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	109514
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/13:10133858
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	asymmetric allylic alkylation; asymmetric baylis-hillman reaction; phosphines; bridged ferrocenes (en)
http://linked.open.../riv/klicoveSlovo	phosphines asymmetric allylic alkylation asymmetric baylis-hillman reaction bridged ferrocenes
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[0F8A5D7EF020]
http://linked.open...i/riv/nazevZdroje	Organometallics
http://linked.open...in/vavai/riv/obor	CA
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...vavai/riv/projekt	Homologous functional phosphinoferrocene ligands for coordination chemistry and catalysis
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	32
http://linked.open...iv/tvurceVysledku	Císařová, Ivana Štěpnička, Petr Škoch, Karel
http://linked.open...ain/vavai/riv/wos	000314332100032
http://linked.open...n/vavai/riv/zamer	Nové molekulární systémy pro pokročilé aplikace prospěšné pro zdraví a šetrné k životnímu prostředí
issn	0276-7333
number of pages	13 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/om3011245
http://localhost/t...ganizacniJednotka	11310

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