Stereoselectivity of macrocyclic ring-closing olefin metathesis.
[reaction: see text] Macrocyclic ring-closing olefin metathesis using ruthenium catalyst 3 was performed to produce a 14-membered lactone. The E/Z ratio of lactone was high regardless of the R group (auxiliary) or the initial alkene stereochemistry. A kinetic study demonstrates that the high E/Z ratio is due to secondary metathesis reactions that isomerize the product to the thermodynamic E/Z ratio.
Lee
C W
CW
The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Grubbs
R H
RH
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007700:Kinetics; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D012428:Ruthenium; D013237:Stereoisomerism; D013816:Thermodynamics
D000475:Alkenes; D007783:Lactones; D012428:Ruthenium