Enantioselective Fluorination of α-Substituted β-Diketones Using β,β-Diaryl Serines
Samira Poorsadeghi1, Katsuki Endo1, Satoru Arimitsu1
1Department of Chemistry, Biology and Marine Science, University of the Ryukyus, Senbaru 1, Nishihara, Nakagami, Okinawa 903-0213, Japan.
Abstract:
We report the enantioselective fluorination of α-substituted β-diketones using β,β-diaryl serines as a primary amine organocatalyst. The reaction affords the corresponding fluorinated products in yields of 74 to 99% with excellent enantioselectivity (75-95% ee). Moreover, for synthetic applications, the diol, aldols, and the allylic fluoride were synthesized from 2a, maintaining excellent enantioselectivity (94% ee). The control experiment reveals that the CO2H group of the β,β-diaryl serines plays an important role in inducing the high enantioselectivity.
More Related Videos
09:58Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
α-Alkylation of Ketones via Enolate Ions
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Base-Promoted α-Halogenation of Aldehydes and Ketones
