About: Polyfunctional beta-Dicarbonyl Compounds by Michael Addition Reactions of Ester Enolates to alpha-Benzylidene and alpha-Alkylidene-beta-dicarbonyl Compounds

Facets (new session)
Description
Metadata
Settings
- owl:sameAs
- Inference Rule:

About: Polyfunctional beta-Dicarbonyl Compounds by Michael Addition Reactions of Ester Enolates to alpha-Benzylidene and alpha-Alkylidene-beta-dicarbonyl Compounds 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
Description	The scope and stereoselectivity of the Michael addition of ester enolates to a-benzylidene and a-alkylidene beta-dicarbonyl compounds was studied. Most substrates reacted in good to excellent yields. Michael acceptors bearing carboxylic functionalities reacted directly in the beta-position, whereas aldol and Michael addition competed with unsaturated ketones. The diastereoselectivity of the process is dependent on the substitution pattern of the Michael acceptor and the geometry of the enolate. (Z)-Enolates add to unsaturated malonates or dibenzoylmethane derivatives with good anti-selectivity, whereas (E)-enolates afforded the syn-diastereomers predominately. Unsaturated nitriles and Meldrum's acid derivatives reacted with low diastereoselectivity. A stereochemical model is proposed that accounts for all experimental results and allows the stereochemical outcome to be predicted. The scope and stereoselectivity of the Michael addition of ester enolates to a-benzylidene and a-alkylidene beta-dicarbonyl compounds was studied. Most substrates reacted in good to excellent yields. Michael acceptors bearing carboxylic functionalities reacted directly in the beta-position, whereas aldol and Michael addition competed with unsaturated ketones. The diastereoselectivity of the process is dependent on the substitution pattern of the Michael acceptor and the geometry of the enolate. (Z)-Enolates add to unsaturated malonates or dibenzoylmethane derivatives with good anti-selectivity, whereas (E)-enolates afforded the syn-diastereomers predominately. Unsaturated nitriles and Meldrum's acid derivatives reacted with low diastereoselectivity. A stereochemical model is proposed that accounts for all experimental results and allows the stereochemical outcome to be predicted. (en)
Title	Polyfunctional beta-Dicarbonyl Compounds by Michael Addition Reactions of Ester Enolates to alpha-Benzylidene and alpha-Alkylidene-beta-dicarbonyl Compounds Polyfunctional beta-Dicarbonyl Compounds by Michael Addition Reactions of Ester Enolates to alpha-Benzylidene and alpha-Alkylidene-beta-dicarbonyl Compounds (en)
skos:prefLabel	Polyfunctional beta-Dicarbonyl Compounds by Michael Addition Reactions of Ester Enolates to alpha-Benzylidene and alpha-Alkylidene-beta-dicarbonyl Compounds Polyfunctional beta-Dicarbonyl Compounds by Michael Addition Reactions of Ester Enolates to alpha-Benzylidene and alpha-Alkylidene-beta-dicarbonyl Compounds (en)
skos:notation	RIV/61388963:_____/12:00378614!RIV13-AV0-61388963
http://linked.open...avai/predkladatel	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...avai/riv/aktivita	I P Z
http://linked.open...avai/riv/aktivity	I, P(GA203/09/1936), Z(AV0Z40550506), Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika	18
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Pohl, Radek Holan, Martin Jahn, Ullrich
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	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	159543
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/12:00378614
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Michael addition; diastereoselectivity; regioselectivity; enols; dicarbonyl compounds (en)
http://linked.open.../riv/klicoveSlovo	Michael addition diastereoselectivity dicarbonyl compounds regioselectivity enols
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[C0C5DDC3B07E]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...vavai/riv/projekt	Unprecedented Domino Processes Involving the Directed Application of Anionic, Transition Metal-Catalyzed, Radical and Carbocationic Reaction Steps
http://linked.open...UplatneniVysledku	2012
http://linked.open...iv/tvurceVysledku	Císařová, I. Pohl, Radek Jahn, Ullrich Holan, Martin
http://linked.open...ain/vavai/riv/wos	000305078600012
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství Nové molekulární systémy pro pokročilé aplikace prospěšné pro zdraví a šetrné k životnímu prostředí
issn	1434-193X
number of pages	17 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201200077
is http://linked.open...avai/riv/vysledek of	Polyfunctional beta-Dicarbonyl Compounds by Michael Addition Reactions of Ester Enolates to alpha-Benzylidene and alpha-Alkylidene-beta-dicarbonyl Compounds

Faceted Search & Find service v1.16.118 as of Jun 21 2024

Alternative Linked Data Documents: ODE Content Formats:

RDF

ODATA

Microdata

About

OpenLink Virtuoso version 07.20.3240 as of Jun 21 2024, on Linux (x86_64-pc-linux-gnu), Single-Server Edition (126 GB total memory, 58 GB memory in use)
Data on this page belongs to its respective rights holders.
Virtuoso Faceted Browser Copyright © 2009-2024 OpenLink Software