10.1021/jo051854a.s001
David M. Bartley
David M.
Bartley
James K. Coward
James K.
Coward
Regioselective Synthesis of α-Methyl
2-Methyleneglutarate via a Novel
Lactonization−Elimination Rearrangement
American Chemical Society
2006
hydroxymethyl
sequence
Regioselective formation
diester precursor proceeds
Methyl
Regioselective Synthesis
Methyleneglutarate
deprotection
methyl
Lactonization
methyleneglutarate
tandem
silyl
Rearrangement
hydroxymethylcyclopentene
monoacid
2006-01-06 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Regioselective_Synthesis_of_Methyl_2_Methyleneglutarate_via_a_Novel_Lactonization_Elimination_Rearrangement/3245281
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.