116761-01-4

Upstream product

• 406-74-6 tert-butyl α-fluoroacetate 
• 100-52-7 benzaldehyde 
• 72582-66-2 (Z)‐2‐fluoro‐3‐phenylacryloyl chloride 
• 75-65-0 tert-butyl alcohol 
• 107-59-5 tert-Butyl chloroacetate 
• 1075204-18-0 C₁₄H₁₃F₇O₄S 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 910803-59-7 tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate 
• 910803-57-5 tert-butyl (1,3-benzothiazol-2-ylsulfanyl)acetate 

Downstream Products

• 93139-50-5 3-phenylpropionic acid tert-butyl ester 
• 116761-08-1 C₁₂H₁₄FO₂S⁽¹⁺⁾*Cl^(1-) 
• 116761-10-5 (3Z)-1-chloro-3-fluoro-4-phenyl-3-buten-2-one 
• 116761-05-8 C₁₂H₁₃FO₂S 

Relevant academic research and scientific papers

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

: 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.

Exceptionally mild, high-yield synthesis of α-fluoro acrylates

Novel achiral and chiral alkyl α-(1,3-benzothiazol-2-ylsulfonyl)- α-fluoroacetates can be readily synthesized by metalation-fluorination of (1,3-benzothiazol-2-ylsulfonyl)acetates. DBU-mediated condensations of these fluorinated synthons with aldehydes proceed in a facile manner at 0 °C or at room temperature giving high yields of α-fluoro acrylates. Ketones are unreactive under these conditions. The presence of fluorine renders the synthon substantially more reactive compared to the unfluorinated analogue. Reactivity of α-(1,3-benzothiazol-2-ylsulfonyl)-α-fluoroacetate and the Horner-Wadsworth-Emmons reagent (EtO)2P(O)CHFCOOEt has also been compared.

Reaction du methylure de dimethylsulfoxonium avec les ester α-fluoro α-ethyleniques

The reaction of dimethylsulfoxonium methylide with α-fluoro α-ethylenic esters: R1-CH=CF-COOR' leads to the formation of β-keto-sulfoxonium ylides 3: R1CH=CF-CO=C-H-S+(O)(CH3)2.Reaction of ylides 3 with anhydrous HCl, at room temperature, provides β-keto γ,γ-fluoro-ethylenic sulfoxonium salts, whose decomposition, at high temperatures, leads to the formation of fluorinated chloromethyl-ketones: R1-CH=CF-CO-CH2Cl, which are not available by other methods.