173167-75-4

Upstream product

• 78-85-3 2-methylpropenal 
• 108-98-5 thiophenol 
• 102104-40-5 1-Benzenesulfinyl-1-chloro-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propan-2-ol 
• 7205-94-9 chloromethyl phenyl sulfoxide 
• 20521-59-9 1-(N-morpholino)-prop-1-ene 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 102104-42-7 1,2-epoxy-2-methyl-1-phenylsulfinyl-3-(tetrahydropyranyloxy)propane 

Downstream Products

• 13012-61-8 [(3-chloro-2-methylpropyl)sulfanyl]benzene 
• 183381-81-9 Benzyl-[2-methyl-3-phenylsulfanyl-prop-(E)-ylidene]-amine 
• 63365-87-7 (+/-)-2-methyl-3-(phenylthio)propan-1-ol 
• 63048-99-7 2-Methyl-3-phenylthio-1-(1'-phenylthiocycloprop-1'-yl)propan-1-ol 
• 116776-75-1 (S)-3-((2S,3S,4S)-3-Hydroxy-2,4-dimethyl-5-phenylsulfanyl-pentanoyl)-4-isopropyl-oxazolidin-2-one 
• 116805-52-8 (S)-3-((2S,3S,4R)-3-Hydroxy-2,4-dimethyl-5-phenylsulfanyl-pentanoyl)-4-isopropyl-oxazolidin-2-one 
• 1262416-53-4 C₁₃H₁₆OS 
• 116840-15-4 (2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-7-oxo-5-phenylsulfanyl-nonanoic acid methyl ester 
• 116776-77-3 (2S,3S,4S,5R,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-7-oxo-5-phenylsulfanyl-nonanoic acid methyl ester 
• 116776-89-7 (E)-(6S,7S,8R)-7-(tert-Butyl-dimethyl-silanyloxy)-2,4,6,8-tetramethyl-9-phenylsulfanyl-non-3-en-5-one 

Relevant academic research and scientific papers

Synthetic Routes to β-Lactams. Some Unexpected Hydrogen Atom Transfer Reactions

Appropriately substituted xanthate derivatives of N-ethenyl acetamides undergo radical cyclisation to give β-lactams with transfer of the xanthate group.In one case, a cascade of unexpected and unusual hydrogen transfer reactions occurred.

Sulfinyl group as an intramolecular nucleophile: Synthesis of bromohydrins from β-methyl-γ,δ-unsaturated sulfoxides with high 1,2-asymmetric induction

Bromohydrins have been prepared from β-methyl-γ,δ-unsaturated sulfoxides with high regio- and stereoselectivity. The reaction proceeds via neighboring group participation of the sulfinyl moiety with inversion of sulfoxide configuration as proven by an 18O labeling study and x-ray crystallography.

Method for the preparation of tetrahydrobenzothiepines

Among its several embodiments, the present invention provides an improved process for the preparation of tetrahydrobenzothiepine-1,1-dioxide compounds; the provision of a process for preparing a diastereomeric mixture of tetrahydrobenzothiepine-1,1-dioxide compounds from a single diastereomer of such compounds; the provision of a process for the preparation of 3-bromo-2-substituted propionaldehyde compounds; and the provision of a process for the preparation of 3-thio-2-substituted propionaldehyde compounds.

Baker's yeast mediated biohydrogenation of sulphur-functionalised methacrolein derivatives. Stereochemical aspects of the reaction and preparation of the two enantiomers of useful C4 bifunctional chiral synthons

The baker's yeast mediated reduction of sulphur-functionalised methacroleins 11, 15 and 18 leads to the preparation of the bifunctional methyl branched C4 chiral synthons 6 and 7. The stereochemical aspects of the biohydrogenation have been investigated. Both the oxidation state of sulphur and the isomeric position of the double bond affected the enantioselectivity of the reduction strongly, thus, offering access to the two enantiomeric forms of 6 and 7.

Kinetic resolution of primary 2-methyl-substituted alcohols via Pseudomonas cepacia lipase-catalysed enantioselective acylation

The enantioselectivities of lipases from Pseudomonas cepacia (PFL, Amano PS, etc.) towards a series of primary 2-methyl-substituted alcohols using vinyl acetate as the acyl donor in transesterifications in organic solvents were studied. In terms of enantioselectivity, the best results were found for 3-aryl-2-methylpropan-1-ols with enantiomeric ratios (E-values) over 100 in most cases, whereas other 3-substituted primary 2-methylpropan-1-ols generally displayed lower enantioselectivities: 3-cycloalkyl-2-methylpropan-1-ols (E ≈ 20) and 2-methylalkan-1-ols (E ≈ 10). Moving the aryl group closer or further away from the chiral centre resulted in low enantioselectivities: 2-arylpropan-1-ols (E 10), 2-methyl-4-(2-thienyl)butan-1-ol (E = 12), 2-methyl-5-(2-thienyl)pentan-1-ol (E = 3.2) and 2-methyl-6-(2-thienyl)hexan-1-ol (E = 3.8).

β- and γ-lactams by nickel powder mediated 4-exo or 5-endo radical cyclisations. A concise construction of the mesembrine skeleton

N-Alkenyl trichloroacetamides, upon treatment with nickel powder and acetic acid in refluxing 2-propanol undergo reversible 4-exo radical cyclisation. The cyclised radical can be trapped in different ways leading to β-lactams. When the trap is omitted or not efficient enough, unusual irreversible 5-endo cyclisation occurs affording functionalised five-membered lactams. Synthesis of bicyclic γ-lactams has also been examined providing in few steps an access to the Sceletium alkaloids skeleton.

Mn(III)-promoted sulfur-directed 4-exo-trig radical cyclization of enamides to β-lactams

The synthesis of β-lactams vinylated at C-4 from N-(3-phenylthio-1- alkenyl) amides was carried out by Mn(III)-promoted 4-exo-trig radical cyclization followed by β-fragmentative loss of phenylthiyl radical. The effects on the reaction course of different substituents both on enamidic nitrogen atom or double bond were analyzed. The overall reaction was stereoselective, leading to trans azetidinones.

α-Sulfenylalkylation of carbonyl compounds at the α-position via magnesium amide-induced enamine sulfenylalkylation with sulfoxides

The reactions of enamines with sulfoxides bearing α-hydrogens in the presence of a magnesium amide, generated in situ from the reaction of ethylmagnesium bromide with diisopropylamine, afforded the corresponding α-sulfenylalkylated ketones and aldehydes in isolated yields ranging from 39 to 76%. This procedure was successfully extended to the bis(methylthio)methylation with methyl (methylthio)methyl sulfoxide.

Carbonyl-Protected β-Lithio Aldehydes and Ketones via Reductive Lithiation. A General Preparative Method for Remarkably Versatile Homoenolate Equivalents

A general procedure for producing homoenolate equivalents consists of reductive lithiation, induced by 4,4'-di-tert-butylbiphenylide, of carbonyl-protected β-(phenylthio) carbonyl compounds prepared in turn by thiophenol addition to enones or the alkylati