title: Conjugate addition of diethyl 1-fluoro-1-phenylsulfonylmethanephosphonate to α,β-unsaturated compounds.
abstract: Diethyl 1-fluoro-1-phenylsulfonylmethanephosphonate (1) in the presence of cesium carbonate undergoes efficient 1,4-addition to Michael acceptors having terminal double bonds such as α,β-unsaturated ketones, esters, sulfones, sulfoxides, and phosphonates to yield the corresponding adducts in good to excellent yields. In the presence of sodium hydride, 1 reacts with α,β-enones to provide γ-fluoro-γ-phenylsulfonylenol phosphates arising from 1,4-addition followed by phosphonate to phosphate rearrangement.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague, Czech Republic.
authors.forename: Stanislav
authors.initials: S
authors.lastname: Opekar
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.forename: Václav
authors.initials: V
authors.lastname: Eigner
authors.forename: Petr
authors.initials: P
authors.lastname: Beier
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002599:Chalcone / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000475:Alkenes; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D063065:Organophosphonates; D013450:Sulfones; D002599:Chalcone