Regioselective synthesis of alpha-methyl 2-methyleneglutarate via a novel lactonization-elimination rearrangement |
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| Authors: | Bartley David M Coward James K |
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| Institution: | Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA. |
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| Abstract: | reaction: see text] A facile route to the alpha-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 O-silyl 2-(hydroxymethyl)dimethylglutarate. |
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