1075204-33-9Relevant academic research and scientific papers
Asymmetric Synthesis of Alkyl Fluorides: Hydrogenation of Fluorinated Olefins
Ponra, Sudipta,Yang, Jianping,Kerdphon, Sutthichat,Andersson, Pher G.
supporting information, p. 9282 - 9287 (2019/05/28)
The development of new general methods for the synthesis of chiral fluorine-containing molecules is important for several scientific disciplines. We herein disclose a straightforward method for the preparation of chiral organofluorine molecules that is ba
Highly efficient and stereoselective Julia-Kocienski protocol for the synthesis of α-fluoro-α,β-unsaturated Esters and Weinreb amides employing 3,5-bis(trifluoromethyl)phenyl (BTFP) sulfones
Alonso, Diego A.,Fuensanta, Monica,Gomez-Bengoa, Enrique,Najera, Carmen
experimental part, p. 1823 - 1829 (2009/07/11)
: α-Fluoroacetates 3 and Weinreb amide 4, bearing a α-[3,5-bis(trifluoromethyl)phenyl]sulfonyl (BTFP-sulfonyl) group at the α-position, are employed in the highly stereoselective synthesis of α-fluoro-α,β-unsaturated alkenoates and Weinreb amides, respectively. Aromatic and aliphatic aldehydes are condensed under extremely mild and simple reaction conditions using potassium carbonate in dimethylformamide at room temperature under solid-liquid phase-transfer catalysis conditions in good yields and high Z-diastereoselectivities, specially in the case of the fluorinated Weinreb amides. A detailed computational mechanistic study suggests a final non-concerted elimination of sulfur dioxide and 3,5-bis(trifluoromethyl)phenoxide and explains the observed high stereoselectivities for the reaction on the basis of thermodynamic and kinetic considerations.
