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

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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

Accès au document

10.24820/ark.5550190.p010.571

2018_KriefWoutersNorbergKremer_articleVersion finale publiée, 1,97 MB

Link to publication in Scopus

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Équipement

Physico-chimie et caractérisation (PC2)

Johan Wouters (!!Manager) & Carmela Aprile (!!Manager)

Plateforme technologique Caracterisation physico-chimiques

Equipement/installations: Plateforme technolgique

Ensembles de données

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

Ensemble de données

CCDC 923100: 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.cczzkfx, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cczzkfx&sid=DataCite

Ensemble de données

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

Contient cette citation

Krief, A., Wouters, J., Norberg, B., & Kremer, A. (2018). Formalizing the mechanism of the allylic substitution reaction (S_N'): Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes. ARKIVOC, 2018(5), 308-333. https://doi.org/10.24820/ark.5550190.p010.571

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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",

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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

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AU - Norberg, Bernadette

AU - Kremer, Adrian

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