Scope and Mechanism of the (4+3) Cycloaddition Reaction of Furfuryl Cations

It all adds up: Furfuryl alcohols are revealed as direct reaction partners for a wide range of conjugated dienes in a (4+3) cycloaddition motif (see scheme). This novel Lewis acid promoted process gives straightforward access to various polycyclic skeletons containing a seven‐membered ring. A plausi...

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Published inAngewandte Chemie International Edition Vol. 50; no. 50; pp. 11990 - 11993
Main Authors Winne, Johan M., Catak, Saron, Waroquier, Michel, Van Speybroeck, Veronique
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 09.12.2011
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
carbocations
Cationic
Cations
Chemistry
Chemistry, Multidisciplinary
Cycloaddition
DFT calculations
Dienes
furans
Furfuryl alcohol
fused-ring systems
Lewis acid
Mathematical analysis
Physical Sciences
Science & Technology
ALLYL CATIONS
fused-ring systems
FURAN
cycloaddition
STEREOSELECTIVITY
carbocations
furans
INTERMEDIATE
OXYALLYL CATIONS
DFT calculations
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Summary:It all adds up: Furfuryl alcohols are revealed as direct reaction partners for a wide range of conjugated dienes in a (4+3) cycloaddition motif (see scheme). This novel Lewis acid promoted process gives straightforward access to various polycyclic skeletons containing a seven‐membered ring. A plausible cationic stepwise mechanism was confirmed by DFT calculations.
Bibliography:ArticleID:ANIE201104930
Fund for Scientific Research Flanders (FWO)
Research Board of Ghent University
We thank Prof. Gerry Pattenden of the University of Nottingham, and Prof. Pierre De Clercq from Ghent University, for their interest and advice in this study. We also thank undergraduates Maria Gomez Rodriguez, Nick Van Hulle, and Ilaria Villa for preparing and performing initial studies with dienes 16, 18, and 21. The Fund for Scientific Research Flanders (FWO) and the Research Board of Ghent University are acknowledged for financial support. Computational resources and services used in this work were provided by Ghent University.
istex:6BF2B3D5F07DDF11E24FFC064CFC62AB0E01562B
ark:/67375/WNG-W949XGJ5-1
The Fund for Scientific Research Flanders (FWO) and the Research Board of Ghent University are acknowledged for financial support. Computational resources and services used in this work were provided by Ghent University.
16
and
18
,
We thank Prof. Gerry Pattenden of the University of Nottingham, and Prof. Pierre De Clercq from Ghent University, for their interest and advice in this study. We also thank undergraduates Maria Gomez Rodriguez, Nick Van Hulle, and Ilaria Villa for preparing and performing initial studies with dienes
21
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201104930