[2+2] Photocycloaddition of symmetrically disubstituted alkenes to 2(5H)-furanones: Diastereoselective entry to 1,2,3,4-tetrasubstituted cyclobutanes

Sònia Parés; Pedro De March; Josep Font; Ramon Alibés; Marta Figueredo

doi:10.1002/ejoc.201100067

[2+2] Photocycloaddition of symmetrically disubstituted alkenes to 2(5H)-furanones: Diastereoselective entry to 1,2,3,4-tetrasubstituted cyclobutanes

Sònia Parés, Pedro De March, Josep Font, Ramon Alibés, Marta Figueredo

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

13 Citations (Scopus)

Abstract

A study on the [2+2] photochemical cycloaddition of 1,4-difunctionalized 2-butenes to 2(5H)-furanones is presented. These reactions deliver 1,2,3,4-tetrasubstituted cyclobutanes with suitable functionalization in the four side chains for further synthetic elaboration. The effects of the substituents in both the lactone and the 2-butene on the stereoselectivity of the photochemical reaction have been evaluated. Starting from (Z)-2-butenes, under photosensitized conditions, a competitive cis/trans isomerization of the olefin inhibits the cycloaddition process. It was found that the presence of a cis double bond confined within a medium-size ring does not prevent bond rotation in the intermediate 1,4-biradicals. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English
Pages (from-to)	3888-3895
Journal	European Journal of Organic Chemistry
Issue number	20-21
DOIs	https://doi.org/10.1002/ejoc.201100067
Publication status	Published - 1 Jul 2011

Keywords

Cycloaddition
Enantioselectivity
Natural products
Photochemistry
Small ring systems

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@article{502f7291202c48a9b6eaa3e1c0b5f170,

title = "[2+2] Photocycloaddition of symmetrically disubstituted alkenes to 2(5H)-furanones: Diastereoselective entry to 1,2,3,4-tetrasubstituted cyclobutanes",

abstract = "A study on the [2+2] photochemical cycloaddition of 1,4-difunctionalized 2-butenes to 2(5H)-furanones is presented. These reactions deliver 1,2,3,4-tetrasubstituted cyclobutanes with suitable functionalization in the four side chains for further synthetic elaboration. The effects of the substituents in both the lactone and the 2-butene on the stereoselectivity of the photochemical reaction have been evaluated. Starting from (Z)-2-butenes, under photosensitized conditions, a competitive cis/trans isomerization of the olefin inhibits the cycloaddition process. It was found that the presence of a cis double bond confined within a medium-size ring does not prevent bond rotation in the intermediate 1,4-biradicals. Copyright {\textcopyright} 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

keywords = "Cycloaddition, Enantioselectivity, Natural products, Photochemistry, Small ring systems",

author = "S{\`o}nia Par{\'e}s and {De March}, Pedro and Josep Font and Ramon Alib{\'e}s and Marta Figueredo",

year = "2011",

month = jul,

day = "1",

doi = "10.1002/ejoc.201100067",

language = "English",

pages = "3888--3895",

number = "20-21",

}

TY - JOUR

T1 - [2+2] Photocycloaddition of symmetrically disubstituted alkenes to 2(5H)-furanones: Diastereoselective entry to 1,2,3,4-tetrasubstituted cyclobutanes

AU - Parés, Sònia

AU - De March, Pedro

AU - Font, Josep

AU - Alibés, Ramon

AU - Figueredo, Marta

PY - 2011/7/1

Y1 - 2011/7/1

N2 - A study on the [2+2] photochemical cycloaddition of 1,4-difunctionalized 2-butenes to 2(5H)-furanones is presented. These reactions deliver 1,2,3,4-tetrasubstituted cyclobutanes with suitable functionalization in the four side chains for further synthetic elaboration. The effects of the substituents in both the lactone and the 2-butene on the stereoselectivity of the photochemical reaction have been evaluated. Starting from (Z)-2-butenes, under photosensitized conditions, a competitive cis/trans isomerization of the olefin inhibits the cycloaddition process. It was found that the presence of a cis double bond confined within a medium-size ring does not prevent bond rotation in the intermediate 1,4-biradicals. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - A study on the [2+2] photochemical cycloaddition of 1,4-difunctionalized 2-butenes to 2(5H)-furanones is presented. These reactions deliver 1,2,3,4-tetrasubstituted cyclobutanes with suitable functionalization in the four side chains for further synthetic elaboration. The effects of the substituents in both the lactone and the 2-butene on the stereoselectivity of the photochemical reaction have been evaluated. Starting from (Z)-2-butenes, under photosensitized conditions, a competitive cis/trans isomerization of the olefin inhibits the cycloaddition process. It was found that the presence of a cis double bond confined within a medium-size ring does not prevent bond rotation in the intermediate 1,4-biradicals. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KW - Cycloaddition

KW - Enantioselectivity

KW - Natural products

KW - Photochemistry

KW - Small ring systems

U2 - 10.1002/ejoc.201100067

DO - 10.1002/ejoc.201100067

M3 - Article

SN - 1434-193X

SP - 3888

EP - 3895

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 20-21

ER -

[2+2] Photocycloaddition of symmetrically disubstituted alkenes to 2(5H)-furanones: Diastereoselective entry to 1,2,3,4-tetrasubstituted cyclobutanes

Abstract

Keywords

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