About: Syntheses of a Flobufen Metabolite and Dapoxetine Based on Enantioselective Allylation of Aromatic Aldehydes

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About: Syntheses of a Flobufen Metabolite and Dapoxetine Based on Enantioselective Allylation of Aromatic Aldehydes Goto Sponge NotDistinct Permalink

An Entity of Type : http://linked.opendata.cz/ontology/domain/vavai/Vysledek, within Data Space : linked.opendata.cz associated with source document(s)

Attributes	Values
rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1002/ejoc.201301899
Description	The enantioselective allylation of an aromatic aldehyde to give a chiral homoallylic alcohol was employed as the key step in the syntheses of a flobufen metabolite and dapoxetine. In the former case, the homoallylic alcohol moiety (99%ee) was converted into a five-membered lactone ring with good preservation of the optical purity, and the target compound, a flobufen metabolite, was obtained in 95%ee. In the latter case, the homoallylic alcohol moiety (97%ee) was transformed over several steps into a 3-aminopropanol moiety. During the course of the synthesis, the gradual loss of optical purity was observed, and the target compound, dapoxetine, was obtained in 85%ee. The enantioselective allylation of an aromatic aldehyde to give a chiral homoallylic alcohol was employed as the key step in the syntheses of a flobufen metabolite and dapoxetine. In the former case, the homoallylic alcohol moiety (99%ee) was converted into a five-membered lactone ring with good preservation of the optical purity, and the target compound, a flobufen metabolite, was obtained in 95%ee. In the latter case, the homoallylic alcohol moiety (97%ee) was transformed over several steps into a 3-aminopropanol moiety. During the course of the synthesis, the gradual loss of optical purity was observed, and the target compound, dapoxetine, was obtained in 85%ee. (en)
Title	Syntheses of a Flobufen Metabolite and Dapoxetine Based on Enantioselective Allylation of Aromatic Aldehydes Syntheses of a Flobufen Metabolite and Dapoxetine Based on Enantioselective Allylation of Aromatic Aldehydes (en)
skos:prefLabel	Syntheses of a Flobufen Metabolite and Dapoxetine Based on Enantioselective Allylation of Aromatic Aldehydes Syntheses of a Flobufen Metabolite and Dapoxetine Based on Enantioselective Allylation of Aromatic Aldehydes (en)
skos:notation	RIV/00216208:11310/14:10281053!RIV15-MSM-11310___
http://linked.open...avai/riv/aktivita	I P Z
http://linked.open...avai/riv/aktivity	I, P(GAP207/11/0587), Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika	12
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Korotvička, Aleš Nečas, David Kotora, Martin Hessler, Filip
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	48955
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/14:10281053
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	enantioselectivity; aldehydes; allylation; organocatalysis; asymmetric catalysis; synthetic methods (en)
http://linked.open.../riv/klicoveSlovo	allylation enantioselectivity aldehydes asymmetric catalysis synthetic methods organocatalysis
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[106F36B0EEF2]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	4 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...vavai/riv/projekt	Development and Application of Catalysts Based on Chiral Bipyridine Scaffold
http://linked.open...UplatneniVysledku	2014
http://linked.open...v/svazekPeriodika	neuveden
http://linked.open...iv/tvurceVysledku	Kotora, Martin Nečas, David Valterová, Irena Korotvička, Aleš Hessler, Filip
http://linked.open...ain/vavai/riv/wos	000334225900015
http://linked.open...n/vavai/riv/zamer	Nové molekulární systémy pro pokročilé aplikace prospěšné pro zdraví a šetrné k životnímu prostředí
issn	1434-193X
number of pages	6 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201301899
http://localhost/t...ganizacniJednotka	11310

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