Salo, EC;Dayak, KR;Huxford, J;Wei, PH;Peraino, NJ;Kerrigan, NJ

2014

January

Arkivoc

Regioselective synthesis of highly substituted enol esters from ketoketene dimer beta-lactones

Published

1 ()

CATALYST 1,3-DIKETONES DIMERIZATION DERIVATIVES ALDEHYDES ACIDS

285

295

A method for the regioselective synthesis of highly substituted enol esters from ketoketene dimers beta-lactones is described. Methylphenylketene dimer was subjected to a sequential one-pot reaction sequence involving ring-opening with an organolithium to give an enolate intermediate, followed by enolate acylation with an acyl chloride to give a highly substituted enol ester as the final product. Complete regioselectivity for O-acylation of the enolate was observed in all cases. Yields of up to 70% were obtained for the one-pot conversion of ketoketene dimers to highly substituted enol esters.

GAINESVILLE

1551-7004

10.3998/ark.5550190.p008.443