Ruthenium-Catalyzed Coupling of Oxabenzonorbornadienes with Alkynes Bearing a Propargylic Oxygen Atom: Access to Stereodefined Benzonorcaradienes

Stereodefined: The title reaction provides an atom‐economic route to benzonorcaradienes. The diastereoselectivity of the coupling relies upon the structure of the alkene; unsubstituted bicyclic alkenes afforded exclusively exo‐benzonorcaradienes (see scheme) whereas the bicyclic alkenes with substit...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2011-09, Vol.50 (39), p.9062-9065
Main Authors: Tenaglia, Alphonse, Marc, Sylvain, Giordano, Laurent, De Riggi, Innocenzo
Format: Article
Language:English
Subjects:
Alkynes
benzonorcaradienes
coupling reactions
homogeneous catalysis
Ruthenium
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Summary:Stereodefined: The title reaction provides an atom‐economic route to benzonorcaradienes. The diastereoselectivity of the coupling relies upon the structure of the alkene; unsubstituted bicyclic alkenes afforded exclusively exo‐benzonorcaradienes (see scheme) whereas the bicyclic alkenes with substituents at the bridgehead positions resulted in endo‐benzonorcaradienes.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201104589