49833-32-1Relevant 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
Efficient synthesis of racemic and chiral alkenyl sulfoxides by palladium-catalyzed Suzuki coupling
Mancha, Gisela,Cuenca, Ana B.,Rodríguez, Nuria,Medio-Simón, Mercedes,Asensio, Gregorio
experimental part, p. 6901 - 6905 (2010/09/18)
Alkenyl sulfoxide derivatives are obtained in high yields through a palladium-catalyzed Suzuki/Miyaura cross-coupling reaction of racemic and chiral 1-halo sulfoxides with aryl and alkenyl boronic acids. Chiral substrates react with no loss of optical purity and high optical yields. The reaction takes place with different palladium catalysts, such as Pd(PPh3)4 or Pd(OAc)2/DABCO. Although nitrogen ligands like DABCO lead to an active palladium catalyst, they are less effective than the phosphine ones.
Addition of sulfenic acids to monosubstituted acetylenes: A theoretical and experimental study
Aversa, Maria Chiara,Barattucci, Anna,Bonaccorsi, Paola,Contini, Alessandro
experimental part, p. 1048 - 1057 (2010/07/13)
The reaction of benzenesulfenic acid, generated in situ by thermal decomposition of 3-(phenylsulfinyl) propanenitrile, with monosubstituted acetylenes was experimentally and theoretically investigated at the DFT level using the MPW1B95 density functional.
Unexpected conversion of vinyl sulfoxides into carbonyl compounds by means of iodotrimethylsilane
Aversa, Maria C.,Barattucci, Anna,Bonaccorsi, Paola,Bruno, Giuseppe,Giannetto, Placido,Policicchio, Manuela
, p. 4441 - 4445 (2007/10/03)
The unexpected and previously unknown TMSI-promoted conversion of α,β- unsaturated sulfoxides into carbonyl compounds and disulfides is described. It occurs in good yields under mild conditions. The examples provided support the generality and efficiency of this procedure which acts as a good method for removing the sulfinyl group with the advantage of transforming the vinyl sulfoxides into carbonyl compounds. (C) 2000 Elsevier Science Ltd.
Reactions of Vinyl Sulfoxides with Magnesium Amides. One-Pot Synthesis of Symmetrical and Unsymmetrical β-(Dialkylamino) Dithioacetals
Kawakita, Masataka,Yokota, Kouichi,Akamatsu, Hideki,Irisawa, Susumu,Morikawa, Osamu,Konishi, Hisatoshi,Kobayashi, Kazuhiro
, p. 8015 - 8017 (2007/10/03)
Vinyl sulfoxides (PhSOCR1=CHR2: R1 = H, Me, or Ph; R2 = H or Me) were treated with (dialkylamino)magnesium reagents, generated in situ from the reaction of EtMgBr with secondary amines (R3R4NH: R3 = Et, i-Pr, or Bn; R4 = Me, Et, or i-Pr) in refluxing Et2O for 1 h, and stirring at room-temperature overnight gave the corresponding symmetrical β-(dialkylamino) dithioacetals [(PhS)2CR1CHR2NR3R4] in 24-84% yields. When the (diethylamino)magnesium reagent was treated with appropriate thiols (RSH; R = p-ClC6H4 or Bn) prior to the interaction with phenyl vinyl sulfoxide, the corresponding unsymmetrical β-(diethylamino) dithioacetals [(PhS)(RS)CHCH2NEt2] were produced in 63-67% yields.
Contrasting Pathways for the Directed Homogeneous Hydrogenation of Vinyl Sulfoxides and Vinyl Sulfones
Ando, David,Bevan, Christopher,Brown, John M.,Price, David W.
, p. 592 - 594 (2007/10/02)
Rh-complex catalysed directed hydrogenation of (α-hydroxyalkyl)vinyl sulfones follows the same stereochemical course as the corresponding acrylates, via HO-coordination; hydrogenation of the related (α-hydroxyalkyl)vinyl sulfoxides is directed by S-O coor
