Regioselective Synthesis of α-Methyl 2-Methyleneglutarate via a Novel Lactonization−Elimination Rearrangement

2006-01-06T00:00:00Z (GMT) by David M. Bartley James K. Coward
A facile route to the α-methyl ester of 2-methyleneglutarate via a three-step sequence from 3-hydroxymethylcyclopentene is described. Regioselective formation of the monoacid from a diester precursor proceeds via a novel fluoride-mediated, tandem deprotection/rearrangement of <i>O</i>-silyl 2-(hydroxymethyl)dimethylglutarate.