545339-02-4Relevant academic research and scientific papers
A new finding in selective Baeyer-Villiger oxidation of α-fluorinated ketones; a new and practical route for the synthesis of α-fluorinated esters
Kobayashi, Satoru,Tanaka, Hiroaki,Amii, Hideki,Uneyama, Kenji
, p. 1547 - 1552 (2003)
α-Fluorinated esters were effectively prepared by the Baeyer-Villiger oxidation of α-fluorinated ketones with m-chloroperbenzoic acid (m-CPBA) under mild conditions. The yield of the esters was influenced by the choice of solvent, base, and substituent on the aryl group of the ketones. 4-Methoxyphenyl substituted fluoroketones were oxidized almost quantitatively with m-CPBA within 10 min to 12 h at room temperature using 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as a cosolvent with CH2Cl2 (1:1, v/v) and aqueous buffer (KH2PO4-NaOH, pH 7.6) as an additive base. The oxidation reaction rates of α-fluorinated ketones were higher than those of the corresponding non-fluorinated ketones. The fluorine atom at α-position of fluoromethyl aryl ketones enhanced the reactivity in the Baeyer-Villiger oxidation.
Metal-mediated Reformatsky reaction of bromodifluoromethyl ketone and imine
Cao, Chun-Ru,Jiang, Min,Liu, Jin-Tao
, p. 1144 - 1151 (2015/02/19)
The Reformatsky reaction of bromodifluoromethyl ketones and imines took place readily in the presence of Zn/CuCl at room temperature to afford β-amino α,α-difluoro ketones in good yields. Using (S)-tert-butanesulfinyl as a chiral auxil-iary, the asymmetric Reformatsky reaction was also achieved and found to proceed with excellent diastereoselectivities. A plausible model is proposed to account for the high stereoselectivity of the reaction.
