1042717-92-9Relevant articles and documents
One-pot synthesis of (Z)-β-sulfonyl enoates from ethyl propiolate
Downey, C. Wade,Craciun, Smaranda,Neferu, Ana M.,Vivelo, Christina A.,Mueller, Carly J.,Southall, Brian C.,Corsi, Stephanie,Etchill, Eric W.,Sault, Ryan J.
supporting information, p. 5763 - 5765 (2012/10/29)
β-Sulfonyl enoates may be synthesized through a one-pot two-step sequence from ethyl propiolate with good to excellent selectivity for the Z isomer. Trialkylamines catalyze thioconjugate additions of aryl thiols, and alkoxides catalyze the addition of ali
One-pot three-step thioconjugate addition-oxidation-Diels-Alder reactions of ethyl propiolate
Downey, C. Wade,Craciun, Smaranda,Vivelo, Christina A.,Neferu, Ana M.,Mueller, Carly J.,Corsi, Stephanie
supporting information, p. 5766 - 5768 (2012/11/06)
Ethyl propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels-Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.
Efficient copper-catalyzed s-vinylation of thiols with vinyl halides
Kao, Hsin-Lun,Lee, Chin-Fa
supporting information; experimental part, p. 5204 - 5207 (2011/12/04)
The synthesis of vinyl sulfides through the coupling reaction of thiols with vinyl iodides, bromides, and chlorides is described. The thiols can couplewith aryl iodides in the presence of only 0.5mol% Cu2O without the need for an ancillary liga
A green and rapid approach for the stereoselective vinylation of phenol, thiol and amine derivatives in water
Sarrafi, Yaghoub,Sadatshahabi, Marzieh,Alimohammadi, Kamal,Tajbakhsh, Mahmood
supporting information; experimental part, p. 2851 - 2858 (2011/11/06)
The stereoselective formation of C-O, C-S and C-N bonds by the reaction of phenols, thiols and amines with activated alkynes is described. The reactions are successfully conducted in water with excellent yields at room temperature. The lack of organic sol
A new class of potential anti-tuberculosis agents: Synthesis and preliminary evaluation of novel acrylic acid ethyl ester derivatives
Kabir, M. Shahjahan,Namjoshi, Ojas A.,Verma, Ranjit,Polanowski, Rebecca,Krueger, Sarah M.,Sherman, David,Rott, Marc A.,Schwan, William R.,Monte, Aaron,Cook, James M.
experimental part, p. 4178 - 4186 (2010/09/12)
Novel acrylic acid ethyl ester derivatives were synthesized and evaluated as potential agents against Mycobacterium species. A versatile and efficient copper-catalyzed coupling process was developed and used to prepare a library of substituted acrylic acid ethyl ester analogs. Minimum inhibitory concentration assays indicated that two of these compounds 3 and 4 have greater in vitro activity against Mycobacterium smegmatis than rifampin, one of the current, first-line anti-mycobacterial chemotherapeutic agents. Moreover, members of this new class of compounds appear to exhibit a specific anti-mycobacterial effect and do not inhibit the growth of the other Gram-positive or Gram-negative species tested.
A very active Cu-catalytic system for the synthesis of aryl, heteroaryl, and vinyl sulfides
Kabir, M. Shahjahan,Lorenz, Michael,Van Linn, Michael L.,Namjoshi, Ojas A.,Ara, Shamim,Cook, James M.
experimental part, p. 3626 - 3643 (2010/07/14)
Figure presented cis-1,2-Cyclohexanediol (L3) has been shown to be an efficient and versatile bidentate O-donor ligand that provides a highly active Cu-catalytic system. It was more effective than diols such as trans-1,2-cyclohexanediol or ethylene glycol. This commercially available cis-1,2-cyclohexanediol ligand facilitated the Cu-catalyzed cross-coupling reactions of alkyl, aryl, or heterocyclic thiols with either alkyl, aryl, heterocyclic, or substituted vinyl halides. This new catalytic system promoted the mild and efficient stereo- and regiospecific synthesis of biologically important vinyl sulfides. The yields obtained using electron-rich substituted vinyl sulfides with this catalyst system are generally 75-98%. Most importantly, this singular catalyst system is extremely versatile and provides entry into a wide range of sulfides. This method is particularly noteworthy given its mild reaction conditions, simplicity, generality, and exceptional level of functional group tolerance.
Stereo- and regiospecific Cu-catalyzed cross-coupling reaction of vinyl iodides and thiols: A very mild and general route for the synthesis of vinyl sulfides
Kabir, M. Shahjahan,Van Linn, Michael L.,Monte, Aaron,Cook, James M.
scheme or table, p. 3363 - 3366 (2009/05/07)
(Chemical Equation Presented) A mild and efficient method for the copper-catalyzed formation of vinylic carbon-sulfur bonds has been developed. The desired vinyl sulfides are obtained in good to excellent yields, with full retention of stereochemistry. This method is particularly noteworthy given its mild reaction conditions, simplicity, and generality, as well as low cost of the catalyst system.
