63365-87-7

Upstream product

• 56102-14-8 2-methyl-3-(phenylsulfanyl)propanal 
• 5296-21-9 2-(phenylsulfanylmethyl)oxirane 
• 75-24-1 trimethylaluminum 
• 2163-42-0 2-methyl-1.3-propanediol 
• 882-33-7 diphenyldisulfane 
• 777-80-0 methyl 3-(phenylthio)isobutyrate 
• 108-98-5 thiophenol 
• 513-42-8 3-hydroxy-2-methyl-1-propene 

Downstream Products

• 13012-61-8 [(3-chloro-2-methylpropyl)sulfanyl]benzene 
• 121783-49-1 (S)-(+)-2-methyl-3-(phenylthio)propan-1-ol 
• 101212-36-6 (R)-(-)-2-methyl-3-(phenylthio)propan-1-ol 
• 1201761-55-8 C₁₀H₁₄O₂S 
• 366454-91-3 phenyl[(2S)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropan-1-yl]sulfide 
• 96689-26-8 1-hydroxy-2-methyl-3-(phenylsulfonyl)propane 

Relevant academic research and scientific papers

Convergent Synthesis of the Dihydropyran Core Containing the C1-C15 Subunit of Sorangicin A Employing Gold(I)-Catalyzed Cyclization of an Allenic Alcohol

A convergent route to the C1-C15 subunit of sorangicin A is disclosed. The key steps include carbon-carbon bond formation using an α-chloro sulfide, regioselective hydrozirconation of an internal alkyne for the preparation of a trisubstituted iodoalkene, allene formation using the Myers-Movassaghi protocol, stereoselective reduction of allylic and propargylic ketones using Noyori's catalyst, and gold(I)-catalyzed cyclization of a β-hydroxy allene to construct the dihydropyran ring.

Stereoselective total synthesis of (-)-nupharamine utilizing an α-chlorosulfide and a sulfinimine for C-C bond formation

An efficient stereoselective synthesis of the nuphar alkaloid, (-)-nupharamine, is reported. The key features include the Lewis acid catalyzed reaction of an α-chlorosulfide with a silyl ketene acetal for C-C bond formation, creation of the stereocenter at C2 by a diastereoselective reaction of allyl indium with a sulfinimine and reductive amination for the introduction of the C6 stereocenter of the piperidine ring.

Cyclopropylation of arylamines at the 2-position with cyclopropylmagnesium carbenoids

Direct cyclopropylation of arylamines at the 2-position with 1-chlorocyclopropyl phenyl sulfoxides was achieved. The reaction of N-lithio arylamines with cyclopropylmagnesium carbenoids, which are generated from 1-chlorocyclopropyl phenyl sulfoxides with

A New, Simple, and Selective Palladium-Catalyzed Cleavage of Triethylsilyl Ethers

(Equation Presented) A simple procedure for the cleavage of triethylsilyl (TES) ethers in the presence of 10 wt % Pd/C in methanol or 95% ethanol is reported. This method allows selective removal of alkyl TES ethers in the presence of aromatic TES ethers or tert-butyldimethylsilyl (TBS) protecting groups.

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).

α-Sulfenyl-Directed Ring-Opening Reactions of Epoxides. 1. Highly Regio- and Stereoselective Reaction with Organo-Aluminum Reagents and Application to the Synthesis of an Aggregation Pheromone

The reaction of 1-phenylthio-2,3-epoxyalkanes with trialkylaluminum showed definite C-2 selectivity for nucleophilic ring-opening and gave C-2 alkylated products exclusively with the complete retention of the configuration at the C-2. In contrast, upon reacting with alkenyl(dialkyl)aluminum, dialkyl(alkynyl)aluminum, or DIBAL, the nucleophilic attack occurred at the C-1 with concomitant rearrangement of the sulfenyl group to the C-2 with the complete inversion of the configuration at the C-2. The reactions of these epoxides were considered to proceed via an episulfonium ion intermediate. Upon applying the present reaction, an aggregation pheromone of African Palm Weevil was stereoselectively synthesized in short steps.