73927-19-2Relevant academic research and scientific papers
Hydrogenative Kinetic Resolution of Vinyl Sulfoxides
Lao, Joan R.,Fernndez-Prez, Hctor,Vidal-Ferran, Anton
supporting information, p. 4114 - 4117 (2015/09/01)
Enantiopure sulfoxides are valuable precursors of organosulfur compounds with broad application in organic and pharmaceutical chemistry. An unprecedented strategy for obtaining highly enantioenriched sulfoxides based on a hydrogenative kinetic resolution using Rh-complexes of phosphine-phosphite ligands as catalysts is reported. After optimization, highly efficient conditions for the kinetic resolution of racemic sulfoxides have been identified. This methodology has been applied to a set of racemic aralkyl or aryl vinyl sulfoxides and allowed the isolation of both recovered and reduced products in excellent yields and enantioselectivities (up to 99% and 97% ee, respectively; 16 examples).
Construction of 1,3-oxathiane ring through Pummerer reaction of γδ- unsaturated sulfinyl compounds
Abe, Hitoshi,Fujii, Hiroyuki,Masunari, Chieko,Itani, Junko,Kashino, Setsuo,Shibaike, Kentaro,Harayama, Takashi
, p. 778 - 785 (2007/10/03)
Several γ,δ-unsaturated sulfinyl compounds were prepared and their reactions with p-toluenesulfonic acid were examined. Conformationally rigid γ,δ-unsaturated sulfinyl compounds such as endo-(alkylsulfinyl)norbornene or 1-(alkylsulfinyl)-2-isopropenylbenzene derivatives afforded 1,3-oxathianes through intramolecular Pummerer rearrangement.
Theoretical and experimental analyses of the deprotonation of thiirane S-oxides: The stereoselective formation of trans-alkyl- and gem-silylethenesulfenate anions
Refvik, Mitchell D.,Froese, Robert D. J.,Goddard, John D.,Pham, Hung H.,Pippert, Mark F.,Schwan, Adrian L.
, p. 184 - 192 (2007/10/02)
Experimental and theoretical studies of the regioselective deprotonation of thiirane S-oxides are reported. Experimentally under the reaction conditions of LiHMDS/THF/-78°C with anti-alkylthiirane S-oxides or anti-silylthiirane S-oxides as starting materials, the products of ring-opening are (E)-2-alkylethenesulfenate and 1-silylethenesulfenate anions, respectively. Experiments involving deuterium labeling clearly indicate that a regioselective deprotonation reaction was followed by a stereoselective ring-opening. Ab initio methods at both the Hartree-Fock and M?ller-Plesset perturbation theory levels with the 6-31+G(d) basis set were used to examine both lithiated methyl- and silylthiirane S-oxides. Of the possible anti-substituted species, the coordination of the lithium anti to the methyl and gem to the silyl is predicted to be the most stable. These stable intermediates with the lithium syn to the sulfoxide could ring-open to yield the experimentally observed products.
The Selective Generation of trans-Substituted Lithium and Sodium Ethenesulfenate Anions
Schwan, Adrian L.,Pippert, Mark F.,Pham, Hung H.,Roche, Michael R.
, p. 1312 - 1314 (2007/10/02)
The reaction of anti-alkyl thiirane S-oxides 1 with hindered amide bases affords trans-substituted ethenesulfenate anions via a deprotonation-ring-opening sequence.
