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

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Lacombe,  Fabrice
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Radkowski,  Karin
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Seidel,  Günter
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

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.


Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-96B7-8
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.