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].
Hanessian
Stephen
S
Department of Chemistry, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montréal, Québec H3C 3J7, Canada.
Giroux
Simon
S
Larsson
Andreas
A