52072-17-0Relevant academic research and scientific papers
Directed addition of sulfur-stabilised carbanions to 1,2,3-trisubstituted aziridines
Craig, Donald,Lu, Pengfei,Mathie, Tanya,Tholen, Niels T.H.
experimental part, p. 6376 - 6382 (2010/10/19)
Thioether and sulfone-stabilised carbanions possessing varying functional groups enter into highly regioselective, stereospecific ring-opening reactions with vinyl- and hydroxymethyl-substituted aziridines. Some derivatisation reactions of the adducts are
Cyclopentannulation of enones with organocuprate reagents containing an acetal or an orthoester function
Ding, Pingyu,Ghosez, Léon
, p. 1565 - 1571 (2007/10/03)
1,1-Dimethyl-3-(phenylthio)-propane 4 was deprotonated with t-BuLi, then converted to the corresponding organocuprate reagent which, in the presence of HMPA and TMSCI, was added to a variety of enones to give the corresponding silylenol ethers 7. These were cyclised without purification upon acidic conditions to give the cyclopentannulation products 9. A similar result was obtained with the corresponding orthoester reagent 6. This cyclopentannulation sequence is applicable to a wide variety of enones except for those bearing substituents near the reacting centre.
Template-directed intramolecular C-glycosidation. Total synthesis of 2,3-dideoxy-D-manno-2-octulopyranosonic acid
Craig, Donald,Pennington, Mark W.,Warner, Peter
, p. 5815 - 5818 (2007/10/02)
The total synthesis of the KDO-inhibitor 2,3-dideoxy-D-manno-2-octulopyranosonic acid (2-deoxy-KDO) starting from TBDPS-protected (S)-glycidol and 3,3-dimethoxy-1-(phenylsulfonyl)-propane is described. The key steps are silver(I) trifluoromethylsulfonate-
Heteroatom-Directed Allylic Substitution and Rearrangement Reactions
Hagen, James P.,Harris, Joseph J.,Lakin, Danielle
, p. 782 - 787 (2007/10/02)
Alcoholic, phenolic, and thiolic nucleophiles attack 3-chloro-1-methoxypropene (1) exclusively at C-1 in the presence of N,N-diisopropylethylamine.The reaction is formally a high regioselective SN2' process.Some of the oxygen nucleophiles (e.g.
The use of aminoiminomethanesulfinic acid (thiourea dioxide) under phase transfer conditions for generating organochalcogenate anions. Synthesis of sulfides, selenides and tellurides
Comasseto, J. V.,Lang, E. S.,Ferreira, J. Tercio B.,Simonelli, F.,Correira, V. R.
, p. 329 - 340 (2007/10/02)
A procedure is described which allows for the in situ synthesis of arylalkyl, diaryl and dialkylchalcogenides under phase transfer conditions starting from the corresponding diorganodichalcogenides.The dichalcogenides are reduced by aminoiminomethanesulfinic acid (thiourea dioxide) in alkaline medium and catalyzed by a quaternary ammonium salt.The reduction proceeds easily for diaryl disulfides and diaryl diselenides at a sodium hydroxide concentration of 13percent; diaryl ditellurides require a 50percent sodium hydroxide solution to give the aryl tellurolate anion.The dialkyl diselenides and dialkyl ditellurides are more difficult to reduce.The intermediate arylthiolates and arylselenolates are quenched by alkyl and activated aryl halides to give the corresponding sulfides and selenides in high yield (77-97percent).The aryltellurolates react with alkyl halides giving the aryl alkyl tellurides in 81-96percent yield.The procedure could not be successfully used for the synthesis of dialkylselenides and dialkyl tellurides; low yields and mixture of products were formed.
Synthesis of 3-Acylfurans Using 3-(Phenylthio)propanal Dimethyl Acetal as a New Synthon. Syntheses of Ipomeanine and Isoegomaketone
Watanabe, Eiji,Imai, Naohiro,Inomata, Katsuhiko,Kinoshita, Hideki,Kotake, Hiroshi
, p. 3225 - 3228 (2007/10/02)
It was found that 3-(phenylthio)propanal dimethyl acetal is a very useful starting material for the preparation of 3-acylfuranoterpenes.Syntheses of two naturally-occurring furans, isoegomaketone and ipomeanine were described.
