40110-68-7Relevant academic research and scientific papers
Stereoselective synthesis of (E)-Vinyl Sulfoxides by the Horner-Wittig reaction
Van Steenis, Jan Hein,Van Es, Joseph Johannes Gerardus Steven,Van Der Gen, Arne
, p. 2787 - 2793 (2007/10/03)
The Horner-Wittig reaction of sulfinylmethyl-substituted di-phenylphosphane oxides 1-3 with aldehydes is reported. In a straightforward synthesis, (E)-vinyl sulfoxides 4 (R1 = Ph), 5 (R1 = Me) and 6 (R1=pTol) were formed m
Additive Pummerer reactions of vinylic sulfoxides. Synthesis of γ-hydroxy-α,β-unsaturated esters, α-hydroxyketones, and 2-phenylsulfenyl aldehydes and primary alcohols
Craig, Donald,Daniels, Kevin,MacKenzie, A. Roderick
, p. 11263 - 11304 (2007/10/02)
Treatment of β-monosubstituted vinylic sulfoxides 1 with trifluoroacetic anhydride in dichloromethane gave excellent yields of 1,2-bis(trifluoroacetoxy)thioethers 6. Mildly basic methanolysis of 2-alkyl-substituted 6 gave α-hydroxyaldehydes 11 as monomer-dimer mixtures; similar treatment of the 2-aryl analogues afforded aryl (hydroxymethyl) ketones 12. Compounds 11 underwent Wittig reactions with methoxycarbonylmethylenetriphenylphosphorane to give high yields of γ-hydroxy-α,β-unsaturated esters 13, predominantly as the E-isomers. β-Monosubstituted vinylic sulfoxides 1 possessing a β-aryl group, and β-disubstituted vinylic sulfoxides 3 reacted with trifluoromethanesulfonic anhydride-sodium acetate in acetic anhydride to give 2-(phenylsulfenyl) acylals 14. These gave 2-phenylsulfenyl aldehydes 15 upon basic methanolysis, and the corresponding primary alcohols 16 on reduction with sodium borohydride. Reaction of both geometric isomers of enantiomerically pure vinylic sulfoxide 1o with TFAA gave racemic 6o as a mixture of diastereomers. Reaction of optically pure (E)- and (Z)-1p with trifluoromethanesulfonic anhydride-sodium acetate in acetic anhydride gave acylal 19 in 10.5 and 23% e.e., respectively.
Synthesis of α,β-γ,δ-unsaturated sulfones and sulfoxides via the Horner-Emmons reaction
Jong, B. E. de,Koning, H. de,Huisman, H. O.
, p. 410 - 414 (2007/10/02)
α,β-γ,δ-Unsaturated sulfones and sulfoxides have been prepared via the Horner-Emmons reaction of α,β-unsaturated carbonyl compounds with α-phosphoryl sulfones and sulfoxides.
