About: Enantioselective Allylation of Selected ortho-Substituted Benzaldehydes: A Comparative Study

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About: Enantioselective Allylation of Selected ortho-Substituted Benzaldehydes: A Comparative Study Goto Sponge NotDistinct Permalink

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Attributes	Values
rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1002/ejoc.201403034
Description	We report a systematic study of the allylation of ortho-substituted benzaldehydes under catalysis of a Lewis base (N, N-dioxide), a Lewis acid (Keck allylation), and a Bronsted acid. ortho-Halobenzaldehydes were used as the aldehydic substrates, and special attention was paid to ortho-vinyl and alkynyl benzaldehydes, which might serve as interesting synthons for the preparation of more complex chiral compounds. Similar enantioselectivities were achieved under catalytic conditions. In the case of ortho-halobenzaldehydes, Lewis base catalysis proved to be more efficient, and the highest asymmetric induction for allylation of ortho-fluorobenzaldehyde reached 82% ee, which is comparable to other used catalytic conditions. In cases of ortho-vinylbenzaldehyde, the Keck allylation provided the product in 88% ee. An enantioenriched homoallylic alcohol was used as the starting material for the synthesis of a sertraline intermediate. We report a systematic study of the allylation of ortho-substituted benzaldehydes under catalysis of a Lewis base (N, N-dioxide), a Lewis acid (Keck allylation), and a Bronsted acid. ortho-Halobenzaldehydes were used as the aldehydic substrates, and special attention was paid to ortho-vinyl and alkynyl benzaldehydes, which might serve as interesting synthons for the preparation of more complex chiral compounds. Similar enantioselectivities were achieved under catalytic conditions. In the case of ortho-halobenzaldehydes, Lewis base catalysis proved to be more efficient, and the highest asymmetric induction for allylation of ortho-fluorobenzaldehyde reached 82% ee, which is comparable to other used catalytic conditions. In cases of ortho-vinylbenzaldehyde, the Keck allylation provided the product in 88% ee. An enantioenriched homoallylic alcohol was used as the starting material for the synthesis of a sertraline intermediate. (en)
Title	Enantioselective Allylation of Selected ortho-Substituted Benzaldehydes: A Comparative Study Enantioselective Allylation of Selected ortho-Substituted Benzaldehydes: A Comparative Study (en)
skos:prefLabel	Enantioselective Allylation of Selected ortho-Substituted Benzaldehydes: A Comparative Study Enantioselective Allylation of Selected ortho-Substituted Benzaldehydes: A Comparative Study (en)
skos:notation	RIV/00216208:11310/14:10283180!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	32
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Betík, Robert Kotora, Martin Kadlčíková, Aneta Hessler, Filip Belle, Roman
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	14493
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/14:10283180
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	aldehydes; Bronsted acid; Lewis acids; Lewis bases; allylation; synthetic methods (en)
http://linked.open.../riv/klicoveSlovo	Bronsted acid Lewis bases allylation aldehydes synthetic methods Lewis acids
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[0946430B9C29]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	5 (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	Kadlčíková, Aneta Kotora, Martin Betík, Robert Hessler, Filip Belle, Roman
http://linked.open...ain/vavai/riv/wos	000344624000023
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	8 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201403034
http://localhost/t...ganizacniJednotka	11310

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