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

Université 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
état	Publié - 7 juil. 2018

Empreinte digitale

Bearings (structural)

Enantiomers

Substitution reactions

Carbon

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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

Krief, Alain ; Wouters, Johan ; Norberg, Bernadette ; Kremer, Adrian. / Formalizing the mechanism of the allylic substitution reaction (S_N') : Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes. Dans: ARKIVOC. 2018 ; Vol 2018, Numéro 5. p. 308-333.

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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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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, VOL. 2018, Numéro 5, p. 308-333. https://doi.org/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. / 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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KW - Aryl cyclopentanes

KW - Benzyl selenides

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