Synthesis of Functionalized Pyrans by Domino Metathesis Reaction of Oxabicyclo Derivatives: Dramatic Effect of Remote Substituents on Reactivity and Selectivity

Consecutive ring‐opening/ring‐closing metathesis reactions of oxabicyclo[3.2.1]octene systems that bear an olefinic tether at the bridgehead lead to highly functionalized, spiro‐annulated pyrans (see scheme). The facility of the reaction is greatly influenced by remote substituents.

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2002-12, Vol.41 (23), p.4560-4562
Main Authors: Usher, Lynn C., Estrella-Jimenez, Maria, Ghiviriga, Ion, Wright, Dennis L.
Format: Article
Language:English
Subjects:
cyclization
heterocycles
metathesis
pyrans
ruthenium
Online Access:Get full text
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Summary:Consecutive ring‐opening/ring‐closing metathesis reactions of oxabicyclo[3.2.1]octene systems that bear an olefinic tether at the bridgehead lead to highly functionalized, spiro‐annulated pyrans (see scheme). The facility of the reaction is greatly influenced by remote substituents.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B