55162-82-8Relevant academic research and scientific papers
Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols
Burde, Ameya S.,Karyakarte, Shuklendu D.,Sylvester, Eric D.,Chemler, Sherry R.
supporting information, p. 105 - 108 (2021/01/14)
Bridged bicyclic ketals display a range of bioactivities. Their catalytic enantioselective synthesis from acyclic 1,1-disubstituted alkene diols is disclosed. This reaction combines asymmetric catalysis with a distal radical migration. Alkynes and arenes
Selective hydroboration of equilibrating allylic azides
Liu, Ruzhang,Xu, Jun,Zhang, Yuanyuan
supporting information, p. 8913 - 8916 (2021/09/13)
The iridium(i)-catalyzed hydroboration of equilibrating allylic azides is reported to provide only the anti-Markovnikov product of alk-1-ene isomers in good yields and with good functional group tolerance.
Catalytic Acceptorless Dehydrogenation of Aliphatic Alcohols
Fuse, Hiromu,Mitsunuma, Harunobu,Kanai, Motomu
supporting information, p. 4493 - 4499 (2020/03/05)
We developed the first acceptorless dehydrogenation of aliphatic secondary alcohols to ketones under visible light irradiation at room temperature by devising a ternary hybrid catalyst system comprising a photoredox catalyst, a thiophosphate organocatalyst, and a nickel catalyst. The reaction proceeded through three main steps: hydrogen atom transfer from the α-C-H bond of an alcohol substrate to the thiyl radical of the photo-oxidized organocatalyst, interception of the generated carbon-centered radical with a nickel catalyst, and β-hydride elimination. The reaction proceeded in high yield under mild conditions without producing side products (except H2 gas) from various alcohols, including sterically hindered alcohols, a steroid, and a pharmaceutical derivative. This catalyst system also promoted acceptorless cross-dehydrogenative esterification from aldehydes and alcohols through hemiacetal intermediates.
Protecting-group-free synthesis of hydroxyesters from amino alcohols
Joseph-Valcin, Eve-Marline,Lebel, Hélène,Reynard, Guillaume
supporting information, p. 10938 - 10941 (2020/10/02)
The synthesis of hydroxyesters from carboxylic acids and unprotected amino alcohols in both continuous flow and batch processes is reported. The formation of a transient diazonium species with a dinitrite reagent is key in this transformation. The reaction conditions are compatible with a variety of functional groups.
Bisnucleophilic substitution as a synthetic tool for ready access to the piperidine alkaloids (+)-Connine, (+)-β-conhydrine, (+)-8-ethylnorlobelol, and (-)-halosaline
Raju, Galla,Anitha, Kadimi,Krishna, Palakodety Radha
, p. 937 - 941 (2015/04/27)
Herein we report the stereoselective total synthesis of (+)-connine, (+)-β-conhydrine, (+)-8-ethylnorlobelol, and (-)-halosaline via bisnucleophilic substitution with benzylamine as the key step.
Copper(I)-catalyzed enantioselective nucleophilic borylation of aldehydes: An efficient route to enantiomerically enriched α-alkoxyorganoboronate esters
Kubota, Koji,Yamamoto, Eiji,Ito, Hajime
supporting information, p. 420 - 424 (2015/01/30)
The first catalytic enantioselective nucleophilic borylation of a
Compositions and methods for treating viral infections
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Page/Page column 38, (2015/10/28)
The present invention provides compositions methods for treating susceptible viral infections, especially hepatitis C viral (HCV) infections as well as co infections of HCV with other viruses such as HBV and/or HIV. In one embodiment, the present inventio
Mild deprotection of PMB ethers using tert-butyl bromide
Rival, Nicolas,Albornoz Grados, Arantxa,Schiavo, Lucie,Colobert, Fran?oise,Hanquet, Gilles
, p. 6823 - 6826 (2015/11/27)
A convenient and high yielding method for the cleavage and scavenging of p-methoxybenzyl protecting group of several alcohols using tert-butyl bromide in refluxing acetonitrile is described. Under these mild conditions other protecting groups such as acid sensitive allyl, benzyl, and Me3CPh2Si ethers, or isopropylidene acetals were unchanged. Interestingly, a selective alkoxy-PMB cleavage was observed in the presence of a PMB phenoxy ether.
Selective catalytic oxidation of alcohols, aldehydes, alkanes and alkenes employing manganese catalysts and hydrogen peroxide
Saisaha, Pattama,Buettner, Lea,Van Der Meer, Margarethe,Hage, Ronald,Feringa, Ben L.,Browne, Wesley R.,De Boer, Johannes W.
, p. 2591 - 2603 (2013/10/21)
The manganese-containing catalytic system [MnIV,IV 2O3(tmtacn)2]2+ (1)/carboxylic acid (where tmtacn=N,N′,N′′-trimethyl-1,4,7-triazacyclononane), initially identified for the cis-dihydroxylation and epoxidation of alkenes, is applied for a wide range of oxidative transformations, including oxidation of alkanes, alcohols and aldehydes employing H2O2 as oxidant. The substrate classes examined include primary and secondary aliphatic and aromatic alcohols, aldehydes, and alkenes. The emphasis is not primarily on identifying optimum conditions for each individual substrate, but understanding the various factors that affect the reactivity of the Mn-tmtacn catalytic system and to explore which functional groups are oxidised preferentially. This catalytic system, of which the reactivity can be tuned by variation of the carboxylato ligands of the in situ formed [MnIII,III 2(O)(RCO2)2(tmtacn)2]2+ dimers, employs H2O2 in a highly atom efficient manner. In addition, several substrates containing more than one oxidation sensitive group could be oxidised selectively, in certain cases even in the absence of protecting groups. Copyright
Rate-acceleration in gold-nanocluster-catalyzed aerobic oxidative esterification using 1,2- and 1,3-diols and their derivatives
Yasukawa, Tomohiro,Miyamura, Hiroyuki,Kobayashi, Shu
experimental part, p. 621 - 627 (2011/10/12)
Aerobic oxidation of aldehydes to 1,2- and 1,3-diol monoesters was catalyzed by polymer-incarcerated gold nanoclusters under ambient conditions. The esterification proceeded much faster with 1,2- and 1,3-diols and their derivatives rather than with methanol. Magnum PI: Gold-nanocluster catalysts, PI-Au, that were immobilized on polystyrene-based polymers with cross-linking moieties, were used to catalyze the syntheses of 1,2 and 1,3-diol monoesters and their derivatives from aldehydes. The effect of neighboring-group participation in the esterification reaction is also described. Copyright
