Radical Solution to the Alkylation of the Highly Base-Sensitive 1,1-Dichloroacetone.

Lucile Anthore (1) , Shiguang Li (1) , Lorenzo V. White (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

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.

Domains: Organic chemistry

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, 2015, 17 (21), pp.5320-5323. ⟨10.1021/acs.orglett.5b02681⟩. ⟨hal-01245804⟩