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

Autor:	Alois Fürstner, Günter Seidel, Fabrice Lacombe, Karin Radkowski
Rok vydání:	2004
Předmět:	Diene Enyne Hydrosilylation Stereochemistry Organic Chemistry Cycloalkyne Ring (chemistry) Metathesis Biochemistry chemistry.chemical_compound chemistry Drug Discovery Salt metathesis reaction Alkyne metathesis
Zdroj:	Tetrahedron. 60:7315-7324
ISSN:	0040-4020
DOI:	10.1016/j.tet.2004.05.042
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6987a239c39e871383ea8358eb5ccf82 https://doi.org/10.1016/j.tet.2004.05.042 Zobrazit plný text záznamu Full Text from ScienceDirect