33840-74-3Relevant academic research and scientific papers
A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
, p. 156 - 161 (2021/01/14)
A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.
α-Benzoyloxylation of β-keto sulfides at ambient temperature
Piras, Enrico,Secci, Francesco,Caboni, Pierluigi,Casula, Maria Francesca,Frongia, Angelo
, p. 49215 - 49219 (2017/11/03)
A facile and efficient protocol for the α-benzoyloxylation of β-keto sulfides is presented. This methodology provides a step-economical, mild and practical access to highly functionalized α-O-benzoyloxy substituted β-keto sulfides, including those with quaternary carbons, which are not easily obtained through currently available methods.
A route to benzylic arylsulfoxides from β-ketosulfoxides
Chang, Meng-Yang,Cheng, Yu-Chieh,Chan, Chieh-Kai
, p. 4068 - 4075 (2016/07/06)
The K2CO3-mediated benzylation of β-ketosulfoxides 4 with 2.0?equiv of benzylic halides 5 affords benzylic arylsulfoxides 6 in moderate yields along with trace amounts of chalcones 7. The products 6 are assumed to form in situ intermediates of sulfenate anions from β-ketosulfoxides which are commonly involved in carbon–sulfur bond formation. A plausible mechanism has been proposed.
First synthesis of β-keto sulfoxides by a palladium-catalyzed carbonylative suzuki reaction
Medio-Simon, Mercedes,Mollar, Cristian,Rodriguez, Nuria,Asensio, Gregorio
, p. 4669 - 4672 (2007/10/03)
(Chemical Equation Presented) An unprecedented palladium-catalyzed three-component cross-coupling reaction between α-bromo sulfoxide, carbon monoxide, and aromatic boronic acids provides a new and efficient approach to the synthesis of β-ketosulfoxides. T
Anodic oxidation of chiral sulfinylamines: A new route to highly diastereoselective α-alkylation of piperidine
Turcaud, Serge,Martens, Thierry,Sierecki, Emma,Pérard-Viret, Jo?lle,Royer, Jacques
, p. 5131 - 5134 (2007/10/03)
The anodic oxidation of some chiral non-racemic N-arylsulfinyl piperidines was investigated and for the first time α methoxylated sulfinyl piperidines were obtained. The so-formed compounds are equivalent of chiral N-sulfinyliminiums and used as new inter
Dianion of sulfinylacetone as a synthetic equivalent of β-enolate of propionic acid: A novel synthesis of carboxylic acids from alkyl halides with three-carbon elongation
Satoh, Tsuyoshi,Imai, Kentaro
, p. 602 - 604 (2007/10/03)
The reaction of the dianion of phenylsulfinylacetone with alkyl halides afforded β-keto sulfoxides, which were first chlorinated with hexachloroethane and then treated successively with KH and t-BuLi to give carboxylic acids in three-steps in moderate overall yields from the alkyl halides. This procedure affords a good method for a synthesis of carboxylic acids from alkyl halides with three-carbon elongation.
Convenient formation of 4-hydroxyalk-2-en-1-one functionality via a Knoevenagel-type carbon chain elongation reaction of aldehyde with 1-arylsulfinylalkan-2-one
Nokami,Kataoka,Shiraishi,Osafune,Hussain,Sumida
, p. 1228 - 1232 (2007/10/03)
A highly functionalized four-carbon unit, 4-hydroxyalk-2-en-1-one functionality [R2CH(OH)CH= CHCOR1], was conveniently prepared by a reaction of an aldehyde (R2CH2CHO) with a 1-(arylsulfinyl)alkan-2-one [ArS(O)CH2COR1] in the presence of diethylamine (Knoevenagel condition). Other functional groups, such as carbonyl and hydroxy groups, in both of the alkyl chains (R1, R2) did not prevent this reaction. This reaction was used to conveniently prepare (±)-(11E)-13-hydroxy-10-oxooctadec-11-enoic acid (14), having cytotoxic activity, and its analogues from undec-10-enoic acid in good yield.
Magnesium methoxide complexation in the control of chemical reactions
Baker, S. Richard,Cadman, Michael L. F.,Crombie, Leslie,Edwards, David A. V.,Mistry, Jayshree
, p. 2705 - 2714 (2007/10/03)
The insolubility of complex magnesium chelates makes experimentation difficult, so smaller complexes are used as models for NMR and deuteration studies.Treatment of methyl cyanoacetate with magnesium methoxide however does not give a simple chelate but a novel kinetic Claisen condensation product, methyl 2,4-dicyano-3-hydroxybut-2-enoate, sequestrated as its magnesium-derivative.Replacement of magnesium methoxide by the non-chelating base sodium methoxide gives the known thermodynamic 1,2-addition product, dimethyl 3-amino-2-cyanopent-2-enedioate.A crossed Claisen product, dimethyl 2-cyano-3-hydroxybut-2-enedioate, has been obtained from diethyl oxalate and methyl cyanoacetate in the presence of magnesium methoxide.However, replacement of the oxalate by phenyl cyanomethyl sulfoxide gives a crossed 1,2-addition product, methyl 3-amino-2-cyano-4-phenylsulfinylbut-2-enoate.Reactions between phenyl cyanomethyl sulfoxide or phenylsulfinylacetone and methyl 2-methoxymethyleneacetoacetate are carried out in the presence of varying amounts of sodium and magnesium methoxides.The products are pyrones, pyridones and aminobenzoates.When sodium methoxide is used in the phenylsulfinylacetone reaction the major product is a pyridine, but with magnesium methoxide it is a hydroxyaminobenzoate.This dichotomy may be explained as a consequence of magnesium complexation by the substrate.
OXIDATION OF SULFIDES BY IODYLARENES IN THE PRESENCE OF VANADYL ACETONYLACETONATE AS A CATALYST
Barret, R.,Pautet, F.,Bordat, P.,Tinland, B.,Daudon, M.
, p. 31 - 34 (2007/10/02)
Key words: Sulfide oxidation; sulfoxide; iodylarene; vanadyl acetylacetonate.Iodylbenzene is a poor oxidant of sulfur, but in the presence of vanadyl acetylacetonate, sulfides are converted into sulfoxides, sulfones and S-dealkylated products.To improve the selectivity and the yield of this reaction, different substituted iodylarenes are used.The N-(paraiodylphenyl) palmitoylamid is a promising oxidant for synthetic purposes.
Switching of the Direction of Enzyme-Mediated Oxidation and Reduction of Sulfur-Substituted 2-Propanols and 2-Propanones
Ohta, Hiromichi,Kato, Yasuo,Tsuchihashi, Gen-ichi
, p. 2735 - 2739 (2007/10/02)
Incubation of 1-(phenylsulfenyl)-2-propanone with Corynebacterium equi IFO 3730 grown on hexadecane at pH 6.5 afforded the corresponding 1-substituted S propanols. 1-(Phenylsulfinyl)-2-propanone was also reduced by the microorganism, the product being aff
