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-alpha-dichloroketones, relying on the degenerative addition transfer of (S)-[3,3dichloro-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 shipped dienoic acid and methyl E,E-dienoates.
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Submitted on : Thursday, December 17, 2015 - 4:32:36 PM
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Lucile Anthore, Shiguang Li, Lorenzo V. White, Samir Z. Zard. Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone.: Application to the Synthesis of Z-Alkenoates and E,E-Dienoates. Organic Letters, American Chemical Society, 2015, 17 (21), pp.5320-5323. ⟨10.1021/acs.orglett.5b02681⟩. ⟨hal-01245804⟩

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