Experimental and Theoretical Study on the Olefin Metathesis of Alkenyl Baylis−Hillman Adducts Using Second-Generation Grubbs Catalyst

We have investigated the olefin metathesis from alkenyl Baylis−Hillman adducts using second-generation Grubbs catalyst. In the experiment, the ring-closing metathesis (RCM) product could not be found, while the cross-metathesis (CM) products were found. The computational studies provided consistent explanations for the experimental result. The most limiting factor for the RCM process using second-generation Grubbs catalyst is caused by the high strain and steric effect in the metallacyclobutane intermediates.