67652-99-7Relevant academic research and scientific papers
Exploiting Substrate Diversity for Preparing Synthetically Valuable Sulfoxides via Asymmetric Hydrogenative Kinetic Resolution
Fernández-Pérez, Héctor,Grabulosa, Arnald,Lao, Joan R.,Vidal-Ferran, Anton
supporting information, (2020/07/24)
A detailed study is disclosed on the Rh-mediated hydrogenative kinetic resolution of α,β-unsaturated sulfoxides with alkyl and aryl substituents at the α-, E- and Z-positions of the double bond. This stereoselective catalytic methodology has enabled the p
Aryl sulfoxides from aliyi sulfoxides via [2,3]-sigmatropic rearrangement and domino Pd-catalyzed generation/ arylation of sulfenate anions
Bernoud, Ellse,Le Duc, Gaetan,Bantrell, Xavier,Prestat, Guillaume,Madec, David,Poll, Giovanni
scheme or table, p. 320 - 323 (2010/03/24)
(Figure presented) Allylic sulfoxides, via [2,3]-sigmatropic rearrangement and oxidative addition of the resulting allylic sulfonate esters to Pd(0), are found to be excellent precursors of sulfenate anions. This hitherto unknown reactivity is applied in a new Pd(0)-catalyzed domino sequence involving sulfonate anion generation followed by arylation to afford aryl sulfoxides.
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
Preparation of Some Novel Butyl, Butenyl, Butadienyl and Bytynyl Sulfone Electrophiles for Use in Enolate Trapping Studies
Loughlin, Wendy A.,Haynes, Richard K.
, p. 651 - 662 (2007/10/02)
The preparation of some novel four-carbon electrophiles and electrophile intermediates is described.Thus, the chlorobutenyl sulfone (5), the iodobutynyl sulfone (6) and the hitherto unreported chlorobutynyl sulfone (4) were prepared.The novel intermediates, containing a chelating imidazolyl functionality, the N-methylimidazolyl sulfides (13)-(15) were also prepared.However, they polymerized rapidly, thus preventing further synthetic manipulations.The preparation of the α-(trimethylsilyl)butadienyl sulfones (17) and (18) is described and the mode of formation of the intermediate α-trimethylsilyl sulfides (21) and (22) from the trimethylsilylbutenyl sulfide (27) is discussed.
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.
Structure-Stability Relationships in Unsaturated Sulfur Compounds. I. On the Stable Conformations of Vinyl Sulfoxides
Kimmelma, Reijo
, p. 706 - 710 (2007/10/02)
The conformations of the stable rotamers of alkyl 1-propenyl sulfoxides have been studied in a thermodynamic and a 13C NMR spectroscopic study.The most stable rotamer of the E isomer was found to have anticlinal conformation.In the Z isomer the synclinal conformation is the most probable.
