28495-06-9Relevant articles and documents
Highly substituted enynes via a palladium-catalyzed tandem three carbon-carbon bonds forming reaction procedure from benzyl halides and alkynyl tributyltin reagents
Pottier, Laurent Romain,Peyrat, Jean-Fran?ois,Alami, Mouad,Brion, Jean-Daniel
, p. 4035 - 4038 (2004)
The first report of the palladium-catalyzed cross coupling reaction of benzyl halides with alkynyl tributyltin reagents is described. This unprecedented coupling, which involves in a single reaction a tandem Stille-carbopalladation-Stille sequence allows the formation of three carbon-carbon bonds chemo-, regio- and stereoselectively and provides an efficient synthesis of highly substituted enynes.
Chiral Bifunctional Phosphine Ligand Enabling Gold-Catalyzed Asymmetric Isomerization of Alkyne to Allene and Asymmetric Synthesis of 2,5-Dihydrofuran
Cheng, Xinpeng,Wang, Zhixun,Quintanilla, Carlos D.,Zhang, Liming
supporting information, p. 3787 - 3791 (2019/03/07)
The asymmetric isomerization of alkyne to allene is the most efficient and the completely atom-economic approach to this class of versatile axial chiral structure. However, the state-of-the-art is limited to tert-butyl alk-3-ynoate substrates that possess
Copper(i) iodide catalyzed synthesis of primary propargylic alcohols from terminal alkyne
Kundu, Shrishnu Kumar,Mitra, Kanchan,Majee, Adinath
, p. 13220 - 13223 (2015/02/19)
A highly efficient and practical method for the synthesis of primary propargylic alcohols has been developed using CuI as catalyst and paraformaldehyde as the formaldehyde source. The reaction was performed under mild reaction conditions offering the desired products in good to excellent yields with a variety of terminal alkynes.
Fully substituted pyranones via quasi-heterogeneous genuinely ligand-free migita-stille coupling of iodoacrylates
Kratochv??l, Ji????,Nov??k, Zden??k,Ghavre, Mukund,Nov??kov??, Lucie,R????i??ka, Ale??,Kune??, Ji????,Pour, Milan
supporting information, p. 520 - 523 (2015/03/04)
Migita-Stille coupling of (Z)-?2-iodoacrylates with (E)-?±-stannyl allylic alcohols to furnish 5-alkylidene-4-substituted-5,6-dihydro-2H-pyran-2-ones is efficiently catalyzed by 2% Pd black in DMF, while Pd(PPh3)4 is inactive. Heterogeneous Pd released in solution is most likely responsible for the catalysis. The reaction is applicable to other substrates, without having to resort to ligands, additives, and/or solid support for Pd. The resulting pyranones can be rearranged to fully functionalized pyranones in another single step.
Carbon–carbon bond formation via benzoyl umpolung attained by photoinduced electron-transfer with benzimidazolines
Igarashi, Tomohito,Tayama, Eiji,Iwamoto, Hajime,Hasegawa, Eietsu
supporting information, p. 6874 - 6877 (2019/04/10)
A photoreaction between benzoyl compounds, such as benzoylformate derivatives, and 2-(p-anisyl)-1,3-dimethylbenzimidazoline in the presence of allyl bromide was found to give various allylated alcohols. In the reaction of benzoylformates, α-hydroxy ester enolates, for which the negative charge occurs on the carbonyl carbon of benzoyl (umpolung reactivity), are proposed to be generated as intermediates by electron-transfer from benzimidazolines to the photoexcited benzoylformates; these species react with allyl bromide to produce α-allyl-α-hydroxy esters.
Lewis base-catalyzed reactions of cyclopropenones: Novel synthesis of mono- or multi-substituted allenic esters
Yang, Yuan-Liang,Zhang, Zhen,Zhang, Xiao-Nan,Wang, De,Wei, Yin,Shi, Min
supporting information, p. 115 - 117 (2014/01/06)
The reactions of cyclopropenones with nucleophiles (H2O or methanol) could be catalyzed by nitrogen-containing Lewis bases or phosphorus-containing Lewis bases, affording the corresponding mono- or multi-substituted allenic esters in moderate t
Enantioselective multicomponent synthesis of fused 6-5 bicyclic 2-butenolides by a cascade heterobicyclisation process
Suero, Marcos G.,De La Campa, Raquel,Torre-Fernandez, Laura,Garcia-Granda, Santiago,Florez, Josefa
supporting information; experimental part, p. 7287 - 7295 (2012/07/17)
The successive coupling of an alkoxy(aryl/heteroaryl)carbene complex of chromium with either a ketone or an imide lithium enolate and then a 3-substituted (H, TMS, PhCH2, PhCH2CH2, Me) propargylic organomagnesium reagent h
TFP as a ligand in Au(i)-catalyzed dihydropyran synthesis. Unprecedented rearrangement of dihydropyrans into cyclopentenones
Matouosva, Eliska,Ruzicka, Ales,Kunes, Jiri,Kralova, Jarmila,Pour, Milan
supporting information; experimental part, p. 9390 - 9392 (2011/10/13)
Dihydropyrans have been prepared by the cyclisation of easily accessible propargyl vinyl ethers with (TFP)AuCl/AgBF4 as a catalyst in high yields. These compounds undergo acid-catalysed rearrangement into cyclopentenone derivatives.
Synthesis of substituted anthracenes, pentaphenes and trinaphthylenes via alkyne-cyclotrimerization reaction
Saino, Naoko,Kawaji, Tsuyoshi,Ito, Taichi,Matsushita, Yuko,Okamoto, Sentaro
scheme or table, p. 1313 - 1316 (2010/04/29)
The [2+2+2] cycloaddition reaction of 1,6-diynes 3 with 4-aryl-2-butyn-1-ols 4 and the following oxidation of the resulting benzylic alcohols to the aldehydes 1 and then treatment with an acid catalyst provided annulated anthracenes 2 in good yields.
Analogs of 1-phosphonooxy-2,2-dihydroxy-3-oxo-5-(methylthio)pentane, an acyclic intermediate in the methionine salvage pathway: A new preparation and characterization of activity with E1 enolase/phosphatase from Klebsiella oxytoca
Zhang, Yalin,Heinsen, Melissa H.,Kostic, Milka,Pagani, Gina M.,Riera, Thomas V.,Perovic, Iva,Hedstrom, Lizbeth,Snider, Barry B.,Pochapsky, Thomas C.
, p. 3847 - 3855 (2007/10/03)
The methionine salvage pathway allows the in vivo recovery of the methylthio moiety of methionine upon the formation of methylthioadenosine (MTA) from S-adenosylmethionine (SAM). The Fe(II)-containing form of acireductone dioxygenase (ARD) catalyzes the p
