244610-63-7Relevant academic research and scientific papers
Transition-Metal-Free Radical Hydrotrifluoromethylation of Alkynes
Matcha, Kiran,Antonchick, Andrey P.
supporting information, p. 309 - 312 (2019/01/24)
A combination of readily available and bench-stable CF3SO2Na and tBuOOH was efficiently used for hydrotrifluoromethylation of alkynes. An excellent trans-selectivity was demonstrated in the synthesis of alkenes. The developed mild reaction conditions allow the supression of the competing Meyer–Schuster-type rearrangement.
Heterogeneous Acid-Catalyzed Racemization of Tertiary Alcohols
G?rbe, Tamás,Lihammar, Richard,B?ckvall, Jan -E.
supporting information, p. 77 - 80 (2017/12/07)
Tertiary alcohols are important structural motifs in natural products and building blocks in organic synthesis but only few methods are known for their enantioselective preparation. Chiral resolution is one of these approaches that leaves one enantiomer (50 % of the material) unaffected. An attractive method to increase the efficiency of those resolutions is to racemize the unaffected enantiomer. In the present work, we have developed a practical racemization protocol for tertiary alcohols. Five different acidic resin materials were tested. The Dowex 50WX8 was the resin of choice since it was capable of racemizing tertiary alcohols without any byproduct formation. Suitable solvents and a biphasic system were investigated, and the optimized system was capable of racemizing differently substituted tertiary alcohols.
Au-catalyzed formation of functionalized quinolines from 2-alkynyl arylazide derivatives
Gronnier, Colombe,Boissonnat, Guillaume,Gagosz, Fabien
supporting information, p. 4234 - 4237 (2013/09/12)
A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.
One-pot gold-catalyzed synthesis of azepino[1,2-a]indoles
Cera, Gianpiero,Piscitelli, Stefano,Chiarucci, Michel,Fabrizi, Giancarlo,Goggiamani, Antonella,Ramón, Rubén S.,Nolan, Steven P.,Bandini, Marco
supporting information, p. 9891 - 9895 (2012/10/29)
Indoles from scratch: A gold(I)/N-heterocyclic carbene complex (IPr=1,3-di(isopropylphenyl)imidazol-2-ylidene) was found to be particularly effective as a catalyst, enabling the one-pot synthesis of tricyclic azepinoindoles by an unprecedented cascade reaction. Readily available substrates, high chemoselectivity, good yields, and water as the only stoichiometric by-product are some of the main advantages of this method. Copyright
Construction of highly substituted stereodefined dienes by cross-coupling of α-allenic acetates
Schneekloth Jr., John S.,Pucheault, Mathieu,Crews, Craig M.
, p. 40 - 43 (2007/10/03)
The assembly of highly substituted dienes remains a challenge for organic chemistry. This work represents a strategy for the construction of highly substituted 1,3-dienes by means of a Tsuji-Trost cross coupling between α-allenic acetates and organozinc reagents. The reaction is high yielding, and installs a trisubstituted olefin with E/Z selectivities up to 95:5 favoring the (E) product. A cheap, commercially available palladium precatalyst and a ligand are used to control the E/Z selectivity. Furthermore, an interesting reversal in selectivity is noted in which appropriate choice of ligand may be used to control the outcome of the reaction and favor the (Z) product. Thirteen examples are described, highlighting the substrate scope of the reaction. It is hoped that the straight-forward reaction conditions and high selectivity will make this reaction of broad use in natural product chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Improved ethynylation of nitrocarbonyl derivatives by cerium trichloride assisted addition of ethynyl magnesium bromide
Salgado-Zamora, Hector,Hernandez, Jorge,Campos, Ma. Elena,Jimenez, Rogelio,Cervantes-Cuevas, Humberto,Mojica, Edna
, p. 461 - 465 (2007/10/03)
The addition of the Grignard reagent ethynyl magnesium bromide to nitroarylcarbonyls in the presence of cerium chloride was investigated. Thus, 2- and 4-nitrobenzaldehyde, 2- and 4-nitroacetophenone, 2-nitrocinnamaldehyde and 1-aryl-3-aryl′-2-en-propanones (nitrochalcones 4a-g), gave α-ethynyl-2- and 4-nitrophenylmethanol 2a-b, α-ethynyl-2- and 4-nitrophenyl ethanol 2c-d, trans-1-(2-nitrophenyl)-1-penten-4-yn-3-ol (5) and trans-1-aryl-3-aryl′-1-penten-4-yn-3-ol 6a-g, respectively. It was found that in the absence of the lanthanide, the ethynylation reaction was a low yielding process. WILEY-VCH Verlag GmbH, 1999.
The Resolution of Tertiary α-Acetylene- Acetate Esters by the Lipase from Candida Cylindracea
O'Hagan, David,Zaidi, Naveed A.
, p. 1111 - 1118 (2007/10/02)
The resolution of tertiary alcohols using the Candida cylindracea lipase is explored.In particular strategies are deployed to limit nonenzymatic hydrolysis of the tertiary acetate substrates in buffer, such that a full range of the steric requirements and
