Efficient Allyl to Propenyl Isomerization in Functionally Diverse Compounds with a Thermally Modified Grubbs Second-Generation Catalyst

Heating compounds containing C-allylic appendages in MeOH in the presence of 10 mol % of Grubbs second-generation catalyst at 0.075 M substrate concentration leads to the corresponding 2-propenyl derivatives without further conjugation in the cases of ketones, esters, and lactams. The reaction is applicable to a large variety of functionally relevant terminal olefins, including O- and N-allyl ethers. [reaction: see text].