About: Organocatalytic Preparation of Substituted Cyclopentanes: A Mechanistic Study

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1021/jo4022106
Description	The reaction mechanism of a tandem conjugate addition/alpha-alkylation of enals leading to functionalized cyclopentanes catalyzed by O-trimethylsilyldiphenylprolinol was investigated by mass spectrometry, NMR spectroscopy, and DFT calculations. We have shown that the high stereoselectivity of the reaction depends on the energy discrimination between the two stereoisomers formed by the condensation of the alpha,beta-unsaturated aldehyde (cinnamaldehyde) and the catalyst. The stereoselectivity of this step depends on the solvent used. The experimental activation barriers were determined to be E-a = 25 +/- 7 kJ mol(-1) (Arrhenius equation), Delta H-double dagger = 23 +/- 7 kJ mol(-1) and Delta G(double dagger) = 101 +/- 9 kJ mol(-1) (Eyring equation). The reaction mechanism of a tandem conjugate addition/alpha-alkylation of enals leading to functionalized cyclopentanes catalyzed by O-trimethylsilyldiphenylprolinol was investigated by mass spectrometry, NMR spectroscopy, and DFT calculations. We have shown that the high stereoselectivity of the reaction depends on the energy discrimination between the two stereoisomers formed by the condensation of the alpha,beta-unsaturated aldehyde (cinnamaldehyde) and the catalyst. The stereoselectivity of this step depends on the solvent used. The experimental activation barriers were determined to be E-a = 25 +/- 7 kJ mol(-1) (Arrhenius equation), Delta H-double dagger = 23 +/- 7 kJ mol(-1) and Delta G(double dagger) = 101 +/- 9 kJ mol(-1) (Eyring equation). (en)
Title	Organocatalytic Preparation of Substituted Cyclopentanes: A Mechanistic Study Organocatalytic Preparation of Substituted Cyclopentanes: A Mechanistic Study (en)
skos:prefLabel	Organocatalytic Preparation of Substituted Cyclopentanes: A Mechanistic Study Organocatalytic Preparation of Substituted Cyclopentanes: A Mechanistic Study (en)
skos:notation	RIV/00216208:11310/14:10271744!RIV15-MSM-11310___
http://linked.open...avai/riv/aktivita	I
http://linked.open...avai/riv/aktivity	I
http://linked.open...iv/cisloPeriodika	4
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Veselý, Jan Hybelbauerová, Simona Remeš, Marek Roithová, Jana Tsybizova, Alexandra
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	35140
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/14:10271744
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	thermochemistry; cascade; spectrometry; density; addition-reactions; lossen rearrangement; domino reactions; electrospray-ionization mass; highly enantioselective synthesis; michael/alpha-alkylation reactions (en)
http://linked.open.../riv/klicoveSlovo	thermochemistry spectrometry domino reactions density electrospray-ionization mass cascade addition-reactions highly enantioselective synthesis lossen rearrangement michael/alpha-alkylation reactions
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[842983217C18]
http://linked.open...i/riv/nazevZdroje	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...UplatneniVysledku	2014
http://linked.open...v/svazekPeriodika	79
http://linked.open...iv/tvurceVysledku	Hybelbauerová, Simona Veselý, Jan Remeš, Marek Roithová, Jana Tsybizova, Alexandra
http://linked.open...ain/vavai/riv/wos	000331926900004
issn	0022-3263
number of pages	8 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/jo4022106
http://localhost/t...ganizacniJednotka	11310

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