Formalizing the mechanism of the allylic substitution reaction (SN'): Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes

Alain Krief; Johan Wouters; Bernadette Norberg; Adrian Kremer

doi:10.24820/ark.5550190.p010.571

Formalizing the mechanism of the allylic substitution reaction (S_N'): Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes

Alain Krief, Johan Wouters, Bernadette Norberg, Adrian Kremer

Universite de Namur

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

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Résumé

We report efficient stereoselective and high yielding syntheses of each of the four enantiomers of phenylcyclopentanes bearing a quaternary center and a E-propenyl chain on the adjacent carbon that involves intramolecular allylic substitution reactions. In complement to its synthetic value, this process models the S_N' reaction and allows prediction of its stereochemical outcome.

langue originale	Anglais
Pages (de - à)	308-333
Nombre de pages	26
journal	ARKIVOC
Volume	2018
Numéro de publication	5
Les DOIs	https://doi.org/10.24820/ark.5550190.p010.571
Etat de la publication	Publié - 7 juil. 2018

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10.24820/ark.5550190.p010.571

2018_KriefWoutersNorbergKremer_articleVersion finale publiée, 1,97 MB

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CCDC 923101: Experimental Crystal Structure Determination
KRIEF, A. (Contributeur), Wouters, J. (Contributeur), NORBERG, B. (Contributeur) & Kremer, A. (Contributeur), University of Namur, 7 juil. 2018
DOI: 10.5517/ccdc.csd.cczzkgy, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cczzkgy&sid=DataCite
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CCDC 923103: Experimental Crystal Structure Determination
KRIEF, A. (Contributeur), Wouters, J. (Contributeur), NORBERG, B. (Contributeur) & Kremer, A. (Contributeur), University of Namur, 7 juil. 2018
DOI: 10.5517/ccdc.csd.cczzkj0, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cczzkj0&sid=DataCite
Ensemble de données
CCDC 923102: Experimental Crystal Structure Determination
KRIEF, A. (Contributeur), Wouters, J. (Contributeur), NORBERG, B. (Contributeur) & Kremer, A. (Contributeur), University of Namur, 7 juil. 2018
DOI: 10.5517/ccdc.csd.cczzkhz, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cczzkhz&sid=DataCite
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Contient cette citation

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title = "Formalizing the mechanism of the allylic substitution reaction (SN'): Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes",

abstract = "We report efficient stereoselective and high yielding syntheses of each of the four enantiomers of phenylcyclopentanes bearing a quaternary center and a E-propenyl chain on the adjacent carbon that involves intramolecular allylic substitution reactions. In complement to its synthetic value, this process models the SN' reaction and allows prediction of its stereochemical outcome.",

keywords = "Aryl cyclopentanes, Benzyl selenides, Se/Li exchange, SN' reaction, Stereospecific carbocyclization",

author = "Alain Krief and Johan Wouters and Bernadette Norberg and Adrian Kremer",

year = "2018",

month = jul,

day = "7",

doi = "10.24820/ark.5550190.p010.571",

language = "English",

volume = "2018",

pages = "308--333",

journal = "ARKIVOC",

issn = "1551-7004",

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number = "5",

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Formalizing the mechanism of the allylic substitution reaction (S_N') : Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes. / Krief, Alain ; Wouters, Johan ; Norberg, Bernadette; Kremer, Adrian.

Dans: ARKIVOC, Vol 2018, Numéro 5, 07.07.2018, p. 308-333.

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

TY - JOUR

T1 - Formalizing the mechanism of the allylic substitution reaction (SN')

T2 - Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes

AU - Krief, Alain

AU - Wouters, Johan

AU - Norberg, Bernadette

AU - Kremer, Adrian

PY - 2018/7/7

Y1 - 2018/7/7

N2 - We report efficient stereoselective and high yielding syntheses of each of the four enantiomers of phenylcyclopentanes bearing a quaternary center and a E-propenyl chain on the adjacent carbon that involves intramolecular allylic substitution reactions. In complement to its synthetic value, this process models the SN' reaction and allows prediction of its stereochemical outcome.

AB - We report efficient stereoselective and high yielding syntheses of each of the four enantiomers of phenylcyclopentanes bearing a quaternary center and a E-propenyl chain on the adjacent carbon that involves intramolecular allylic substitution reactions. In complement to its synthetic value, this process models the SN' reaction and allows prediction of its stereochemical outcome.

KW - Aryl cyclopentanes

KW - Benzyl selenides

KW - Se/Li exchange

KW - SN' reaction

KW - Stereospecific carbocyclization

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U2 - 10.24820/ark.5550190.p010.571

DO - 10.24820/ark.5550190.p010.571

M3 - Article

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EP - 333

JO - ARKIVOC

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ER -

Formalizing the mechanism of the allylic substitution reaction (SN'): Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Équipement

Physico-chimie et caractérisation (PC2)

Ensembles de données

CCDC 923101: Experimental Crystal Structure Determination

CCDC 923103: Experimental Crystal Structure Determination

CCDC 923102: Experimental Crystal Structure Determination

Contient cette citation

Formalizing the mechanism of the allylic substitution reaction (S_N'): Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes