Enyne Metathesis for the Formation of Macrocyclic 1,3-Dienes

Enyne Metathesis for the Formation of Macrocyclic 1,3-Dienes

Macrocyclic 1,3-dienes of a variety of ring sizes are formed in good yield via enyne metathesis. Both endo- and exo-products are observed depending on the size of the macrocycle. In general, 10-membered rings and smaller give exo-products, while 12-membered rings and larger give endo-products. The e...

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Veröffentlicht in:Journal of the American Chemical Society 2003-08, Vol.125 (32), p.9582-9583
Hauptverfasser: Hansen, Eric C, Lee, Daesung
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Chemistry
Cyclization
Cycloparaffins - chemical synthesis
Cycloparaffins - chemistry
Exact sciences and technology
Heterocyclic Compounds - chemical synthesis
Organic chemistry
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Zusammenfassung:Macrocyclic 1,3-dienes of a variety of ring sizes are formed in good yield via enyne metathesis. Both endo- and exo-products are observed depending on the size of the macrocycle. In general, 10-membered rings and smaller give exo-products, while 12-membered rings and larger give endo-products. The endo/exo selectivity and the E/Z ratio of the diene products can be further controlled by the presence of ethylene in the reaction.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja036374k