title: Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone. Application to the Synthesis of Z-Alkenoates and E,E-Dienoates.
abstract: A simple radical-based route to gem-α-dichloroketones, relying on the degenerative addition transfer of (S)-[3,3-dichloro-2-oxopropyl]-O-ethyl dithiocarbonate (xanthate), is described. The adducts can then be converted into Z-enoates by exposure to Et3N in methanol. In the case of certain substrates, it was possible to form skipped dienoic acid and methyl E,E-dienoates.
authors.affiliation: Laboratoire de Synthèse Organique, CNRS UMR 7652 Ecole Polytechnique , Palaiseau 91128 Cedex, France.
authors.forename: Lucile
authors.initials: L
authors.lastname: Anthore
authors.affiliation: Laboratoire de Synthèse Organique, CNRS UMR 7652 Ecole Polytechnique , Palaiseau 91128 Cedex, France.
authors.forename: Shiguang
authors.initials: S
authors.lastname: Li
authors.affiliation: Laboratoire de Synthèse Organique, CNRS UMR 7652 Ecole Polytechnique , Palaiseau 91128 Cedex, France.
authors.forename: Lorenzo V
authors.initials: LV
authors.lastname: White
authors.affiliation: Laboratoire de Synthèse Organique, CNRS UMR 7652 Ecole Polytechnique , Palaiseau 91128 Cedex, France.
authors.forename: Samir Z
authors.initials: SZ
authors.lastname: Zard