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

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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 SN' reaction and allows prediction of its stereochemical outcome.

langue originaleAnglais
Pages (de - à)308-333
Nombre de pages26
journalARKIVOC
Volume2018
Numéro de publication5
Les DOIs
étatPublié - 7 juil. 2018

Empreinte digitale

Bearings (structural)
Enantiomers
Substitution reactions
Carbon

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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 = "7",
day = "7",
doi = "10.24820/ark.5550190.p010.571",
language = "English",
volume = "2018",
pages = "308--333",
journal = "ARKIVOC",
issn = "1551-7004",
publisher = "Arkat USA",
number = "5",

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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

UR - http://www.scopus.com/inward/record.url?scp=85052636131&partnerID=8YFLogxK

U2 - 10.24820/ark.5550190.p010.571

DO - 10.24820/ark.5550190.p010.571

M3 - Article

AN - SCOPUS:85052636131

VL - 2018

SP - 308

EP - 333

JO - ARKIVOC

JF - ARKIVOC

SN - 1551-7004

IS - 5

ER -