About: Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis

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Description	Bis-ortho- and bis-meta-phenylene homologues of BINOL-based N,N-dimethylphosphoramidites were prepared from the corresponding diols by treatment with hexamethyltriaminophosphane. Phosphoramidites derived from bulkier secondary amines were synthesized by 5-phenyl-1H-tetrazole-promoted amine exchange. All the phosphoramidites were obtained as single diastereomers. Their configurations at the C(naphthyl)?C(phenyl) axes were determined by vibrational circular dichroism (VCD) spectroscopy. Preliminary testing of the ligands in copper-catalyzed conjugate addition of diethylzinc to acyclic enones and nitrostyrene gave the corresponding products in up to 74% ee. Bis-ortho- and bis-meta-phenylene homologues of BINOL-based N,N-dimethylphosphoramidites were prepared from the corresponding diols by treatment with hexamethyltriaminophosphane. Phosphoramidites derived from bulkier secondary amines were synthesized by 5-phenyl-1H-tetrazole-promoted amine exchange. All the phosphoramidites were obtained as single diastereomers. Their configurations at the C(naphthyl)?C(phenyl) axes were determined by vibrational circular dichroism (VCD) spectroscopy. Preliminary testing of the ligands in copper-catalyzed conjugate addition of diethylzinc to acyclic enones and nitrostyrene gave the corresponding products in up to 74% ee. (en)
Title	Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis (en)
skos:prefLabel	Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis (en)
skos:notation	RIV/60461373:22340/10:00023356!RIV11-MSM-22340___
http://linked.open...avai/riv/aktivita	Z
http://linked.open...avai/riv/aktivity	Z(MSM6046137307)
http://linked.open...iv/cisloPeriodika	15
http://linked.open...vai/riv/dodaniDat	2011
http://linked.open...aciTvurceVysledku	Julínek, Ondřej Urbanová, Marie Setnička, Vladimír
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	Vysoká škola chemicko-technologická v Praze / Fakulta chemicko-inženýrská
http://linked.open...dnocenehoVysledku	249010
http://linked.open...ai/riv/idVysledku	RIV/60461373:22340/10:00023356
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	binaphthyl; absolute configuration; synthesis; catalysis; vibrational circular dichroism (en)
http://linked.open.../riv/klicoveSlovo	vibrational circular dichroism catalysis absolute configuration synthesis binaphthyl
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[1F47D3371874]
http://linked.open...i/riv/nazevZdroje	Tetrahedron Letters
http://linked.open...in/vavai/riv/obor	CB
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...UplatneniVysledku	2010
http://linked.open...v/svazekPeriodika	51
http://linked.open...iv/tvurceVysledku	Urbanová, Marie Julínek, Ondřej Setnička, Vladimír Mešková, M. Miklášová, N. Putala, M.
http://linked.open...ain/vavai/riv/wos	000276668800010
http://linked.open...n/vavai/riv/zamer	Physico-chemical methods of analysis and characterization of chemical systems and biosystems
issn	0040-4039
number of pages	5 (xsd:int)
http://localhost/t...ganizacniJednotka	22340
is http://linked.open...avai/riv/vysledek of	Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis

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