title: Cross-metathesis between alpha-methylene-gamma-butyrolactone and olefins: a dramatic additive effect.
abstract: [reaction: see text] Olefin cross-metathesis between alpha-methylene-gamma-butyrolactone and terminal olefins is described. Moderate to excellent yields of alpha-alkylidene-gamma-butyrolactones were obtained with high E-stereoselectivity in the presence of low catalyst loading in refluxing CH2Cl2. In addition, the use of various additives was found to have a dramatic effect on the efficiency of the cross-metathesis (CM) process by circumventing the formation of the isomerized byproduct.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI, CNRS, 10 rue Vauquelin, F-75231 Paris Cedex 05, France.
authors.forename: Joëlle
authors.initials: J
authors.lastname: Moïse
authors.forename: Stellios
authors.initials: S
authors.lastname: Arseniyadis
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001688:Biological Products; C014096:alpha-methylene gamma-butyrolactone; D012428:Ruthenium; D015107:4-Butyrolactone