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

University of Namur

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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 S_N' reaction and allows prediction of its stereochemical outcome.

Original language	English
Pages (from-to)	308-333
Number of pages	26
Journal	ARKIVOC
Volume	2018
Issue number	5
DOIs	https://doi.org/10.24820/ark.5550190.p010.571
Publication status	Published - 7 Jul 2018

Keywords

Aryl cyclopentanes
Benzyl selenides
Se/Li exchange
SN' reaction
Stereospecific carbocyclization

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10.24820/ark.5550190.p010.571

2018_KriefWoutersNorbergKremer_articleFinal published version, 1.97 MB

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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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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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SP - 308

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IS - 5

ER -

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

Abstract

Keywords

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Physical Chemistry and characterization(PC2)

CCDC 923103: Experimental Crystal Structure Determination

CCDC 923100: Experimental Crystal Structure Determination

CCDC 923101: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Equipment

Physical Chemistry and characterization(PC2)

Datasets

CCDC 923103: Experimental Crystal Structure Determination

CCDC 923100: Experimental Crystal Structure Determination

CCDC 923101: Experimental Crystal Structure Determination

Cite this

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