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Conjugated Enynes as a New Type of Substrates for Olefin Metathesis

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Center for Molecular Design and Synthesis (CMDS), Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701, Korea
Cite this: Org. Lett. 2003, 5, 17, 3041–3043
Publication Date (Web):July 19, 2003
https://doi.org/10.1021/ol035014z
Copyright © 2003 American Chemical Society
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    Abstract

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    It has been demonstrated for the first time that conjugated enynes can be employed as a facile substrate in olefin metathesis with the use of a bispyridine-substituted ruthenium benzylidene catalyst. Cross-metathesis of the enynes with alkenes turns out to proceed with preferential formation of (Z)-isomers over (E)-isomers up to >25:1 in moderate to good yields. The intramolecular version of conjugated enynes affords novel butadienyl cycloalkenes, which are a highly useful synthetic building blocks, in acceptable yields.

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    Detailed experimental procedures and spectroscopic data for all new compounds obtained in this study. This material is available free of charge via the Internet at http://pubs.acs.org.

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