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.