Cross-metathesis between alpha-methylene-gamma-butyrolactone and olefins: a dramatic additive effect.
[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.
Moïse
Joëlle
J
Laboratoire de Chimie Organique, ESPCI, CNRS, 10 rue Vauquelin, F-75231 Paris Cedex 05, France.
Arseniyadis
Stellios
S
Cossy
Janine
J
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
D000475:Alkenes; D001688:Biological Products; C014096:alpha-methylene gamma-butyrolactone; D012428:Ruthenium; D015107:4-Butyrolactone