27328-17-2

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 91796-57-5 4-Methyl-benzenesulfinic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 79-24-3 Nitroethane 
• 36832-47-0 vinyl-4-tolylsulfoxide 
• 16336-54-2 p-tolyl vinyl sulfide 
• 106-45-6 para-thiocresol 
• 50-00-0 formaldehyd 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 1017-88-5 dimethyldiphenylphosphonium iodide 
• 2065-66-9 methyl-triphenylphosphonium iodide 

Downstream Products

• 134356-81-3 (1S,4S,5R)-5-((S)-Toluene-4-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-2-ene 
• 134356-80-2 (1R,4R,5R)-5-((S)-Toluene-4-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-2-ene 
• 208989-15-5 (1S,5S,6R,R_S)-3-(p-fluorophenyl)-N-methyl-6-(p-tolylsulfinyl)-8-azabicyclo<3.2.1>oct-3-en-2-one 
• 208989-13-3 (1S,5S,6R,R_S)-N-methyl-6-(p-tolylsulfinyl)-3-p-tolyl-8-azabicyclo<3.2.1>oct-3-en-2-one 
• 197590-75-3 (1S,5S,6R,R_S)-N-methyl-3-phenyl-6-(p-tolylsulfinyl)-8-azabicyclo<3.2.1>oct-3-en-2-one 
• 1950-69-2 toluene-p-sulfonyl bromide 
• 134297-23-7 (1R,4R,5R)-5-((R)-Toluene-4-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-2-ene 
• 134356-78-8 (1S,4S,5R)-5-((R)-Toluene-4-sulfinyl)-7-oxa-bicyclo[2.2.1]hept-2-ene 

Relevant academic research and scientific papers

An efficient resolution of (±)-p-tolylvinylsulfoxide using (-)-menthol

The preparation of enantiopure (+)-(R)(S) and (-)-(S)(S)-p- tolylvinylsulfoxide using (-)-menthol as a resolving agent is described.

Hydrogenative Kinetic Resolution of Vinyl Sulfoxides

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).

Stereoselective synthesis of racemic and optically active E-vinyl and E- dienyl sulfoxides via Wittig reaction of α-sulfinyl phosphonium ylides

A series of α-sulfinyl phosphonium ylides have been obtained in the reaction of phosphonium mono- and diylides with sulfinic acid esters. The use of (-)-(S)-menthyl p-toluenesulfinate in this reaction afforded the corresponding (S)-((p-tolylsulfinyl)methyl)triphenylphosphonium ylide. The Wittig reaction of these ylides with saturated and unsaturated aldehydes resulted in the formation of racemic and optically active (+)-(R)-vinyl and dienyl sulfoxides with the E-geometry. The synthesis of (+)-(R)-((p- tolylsulfinyl)methyl)triphenylphosphonium iodide as a precursor of the optically active ylide has also been described.

Enantioselective additive pummerer-type reaction in chiral, non-racemic vinyl sulfoxides induced by O-silylated ketene acetal

Treatment of chiral, non-racemic vinyl sulfoxides with O-silylated ketene acetal in the presence of a catalytic amount of zinc chloride in tetrahydrofuran resulted in an enantioselective Pummerer-type reaction, affording a considerable yield of the corresponding enantiomerically enriched methyl 4-siloxy-4-sulfenylbutyrate in 78-82% ee.

Asymmetric Induction in the Michael Reaction by Means of Chiral Phase-transfer Catalysts derived from Cinchona and Ephedra Alkaloids

Asymmetric induction in the Michael reaction has been achieved using alkaloidonium salts in a two-phase system with optical yields of up to 36 and 26percent in the addition to αβ-unsaturated ketones of thiols and nitroalkanes respectively.The presence of a hydroxy-group β to the 'onium function is essential to achieve substantial asymmetric syntheses.