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  (E)-Cycloalkenes and (E,E)-cycloalkadienes by ring closing diyne- or enyne–yne metathesis/semi-reduction

Lacombe, F., Radkowski, K., Seidel, G., & Fürstner, A. (2004). (E)-Cycloalkenes and (E,E)-cycloalkadienes by ring closing diyne- or enyne–yne metathesis/semi-reduction. Tetrahedron, 60(34), 7315-7324. doi:10.1016/j.tet.2004.05.042.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-000F-96B7-8 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0028-1422-0
Genre: Journal Article

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 Creators:
Lacombe, Fabrice1, Author           
Radkowski, Karin1, Author           
Seidel, Günter1, Author           
Fürstner, Alois1, Author           
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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Free keywords: olefins; cycloalkyne; enyne; diene; metathesis
 Abstract: A concise, practical and stereoselective entry into macrocyclic (E)-alkenes is outlined comprising a sequence of ring closing alkyne metathesis (RCAM), trans-selective hydrosilylation of the resulting cycloalkynes catalyzed by [Cp∗Ru(MeCN)3]PF6, and a protodesilylation of the ensuing vinylsilanes with AgF in aq. THF/MeOH. Moreover, the first examples of intramolecular enyne–yne metathesis reactions catalyzed by the Schrock alkylidyne complex (tBuO)3W≡CCMe3 are reported; the resulting cyclic enynes can be converted along similar lines into the corresponding (E,E)-configured 1,3-dienes in good overall yields. Cycloalkyne 4 and the (E)-configured cyclic olefins 6 and 21 were characterized by X-ray crystallography.

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Language(s): eng - English
 Dates: 2004-05-182004-04-022004-05-192004-06-092004-08-16
 Publication Status: Published in print
 Pages: 10
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 218310
DOI: 10.1016/j.tet.2004.05.042
ISI: 000223090800023
 Degree: -

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Title: Tetrahedron
  Other : Tetrahedron
Source Genre: Journal
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Publ. Info: Oxford : Pergamon
Pages: - Volume / Issue: 60 (34) Sequence Number: - Start / End Page: 7315 - 7324 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/954925448773