1149578-22-2

Upstream product

• 1149578-18-6 (1,3-benzothiazol-2-ylsulfanyl)fluoromethyl phenyl ketone 
• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 
• 13944-95-1 2-(phenacylsulfanyl)-1,3-benzothiazole 
• 331984-42-0 2-(benzo[d]thiazol-2-ylsulfonyl)-1-phenylethan-1-one 
• 149-30-4 2-Mercaptobenzothiazole 
• 321-75-5 α-bromo-α-fluorophenylethanone 

Downstream Products

• 126912-57-0 (Z)-2-fluoro-3-(4-methoxyphenyl)-1-phenyl-2-propen-1-one 
• 1149578-27-7 (Z)-2-fluoro-3-(2-methoxyphenyl)-1-phenyl-2-propen-1-one 
• 1296831-43-0 (S,E)-3-(1-fluoro-2-phenylvinyl)cyclohexanone 
• 1296831-41-8 (R,E)-3-(1-fluoro-2-phenylvinyl)cyclohexanone 

Relevant academic research and scientific papers

High Chemo-/Stereoselectivity for Synthesis of Polysubstituted Monofluorinated Pyrimidyl Enol Ether Derivatives

A novel intramolecular Smiles rearrangement of α-fluoro-β-keto-pyrimidylsulfones (usually used as a carbon nucleophile) was developed, providing a versatile avenue for synthesis of tri/tetra-substituted monofluorinated pyrimidyl enol ethers. Among these, diverse (Z)-monofluorovinylsulfones and sulfinates were efficiently assembled by adding extra electrophile and fine-tuning reaction conditions. The process is triggered by a keto-enol tautomerism from enol oxyanion to pyrimidine 2-carbon, completely different from the classical carbon nucleophilic addition reaction approach.

Asymmetric organocatalytic monofluorovinylations

The development of highly enantio-and diastereoselective organocatalytic monofluorovinylations is presented. Based on the application of β-fluoro-β-keto-benzothiazolesulfones, the formal addition of a monofluorovinylic anion synthon to a range of acyclic and cyclic enones, as well as imines, is shown. These procedures give selective access to both E-and Z-isomers of the monofluorovinylated products, which are isolated as the pure diastereoisomers in good to excellent yields with up to 99% ee. Furthermore, the application of this concept for the formation of highly enantioenriched bicylic compounds containing a monofluorovinyl moiety is also described. In addition, a mechanistic rationale for the observed E:Z-selectivities is presented.

α-fluorovinyl Weinreb amides and α-fluoroenones from a common fluorinated building block

(Chemical Equation Presented) Synthesis and reactivity of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfonyl)fluoroacetamide, a building block for Julia olefination, is reported. This reagent undergoes condensation reactions with aldehydes and cyclic keton