55962-00-0Relevant academic research and scientific papers
Direct anomeric substitution of pyranyl esters using organocopper reagents
Bolitt,Mioskowski,Falck
, p. 6027 - 6030 (1989)
2-Substituted tetrahydropyrans were obtained by direct anomeric substitution of tetrahydropyranyl 2,4-dimethoxybenzoate, using Grignard-derived organocopper reagents.
Direct photochemical cross-coupling between aliphatic acids and BF3K salts
Sun, Zhuming,Tang, Bingqing,Liu, Kevin K.-C.,Zhu, Hugh Y.
supporting information, p. 1294 - 1297 (2020/02/04)
We describe a novel photoredox hetero-coupling reaction of two C (sp3) radicals from aliphatic acids or BF3K salts. The kinetic differences in radical persistence provide cross-selectivity, using an organic photoredox catalyst and an oxidant with visible light. This method exhibits broad scope, including several examples constructing sterically hindered C(sp3)-C(sp3) bonds.
Catalytic and metal-free intramolecular hydroalkoxylation of alkynes
Jean, Alexandre,Rouden, Jacques,Maddaluno, Jacques,De Paolis, Micha?l,Blanchet, Jér?me
, p. 534 - 537 (2019/01/19)
Benzyltrimethylammonium hydroxide act as an efficient metal-free catalyst for the intramolecular hydroalkoxylation of alkynes. Notably, the use of microwave irradiation allowed reaction to operate in only two minutes. Under optimized reaction conditions, linear alkynes bearing aryl and heteroaryl substituents were successfully cyclized with good level of stereoselectivity.
On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet
Chio, Freda K.,Warne, Julie,Gough, Damien,Penny, Mark,Green, Sasa,Coles, Simon J.,Hursthouse, Mike B.,Jones, Peter,Hassall, Lorraine,McGuire, Thomas M.,Dobbs, Adrian P.
supporting information; experimental part, p. 5107 - 5124 (2011/07/31)
While developing new variations of the Prins cyclisation reaction, the effect of the choice of Lewis acid on the outcome of the reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation reac
Cyclopropenium-activated cyclodehydration of diols
Kelly, Brendan D.,Lambert, Tristan H.
, p. 740 - 743 (2011/05/04)
The dehydrative cyclization of diols to cyclic ethers via cyclopropenium activation is described. Using 2,3-diphenylcyclopropene and methanesulfonic anhydride, a series of 1,4-and 1,5-diols are rapidly cyclized to furnish tetrahydrofurans and tetrahydropyrans in high yield. Eleven total substrates are shown, including a gram scale cyclization of a diterpene derivative.
Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes
Zhang, Guozhu,Cui, Li,Wang, Yanzhao,Zhang, Liming
supporting information; experimental part, p. 1474 - 1475 (2010/04/04)
(Chemical Equation Presented) Homogeneous carboamination, carboalkoxylation and carbolactonization of terminal alkenes are realized via oxidative gold catalysis, providing expedient access to various substituted Nor O-heterocycles. Deuterium-labeling studies established the anti nature of the alkene functionalization and the indispensible role of Au(I)/Au(III) catalysis. This study constitutes the first example of catalytically converting C(sp 3)-Au bonds into C(sp3)-C(sp2) bonds in a crosscoupling manner and opens new opportunities to study gold alkene catalysis where alkylgold intermediates can be readily functionalized intermolecularly. Copyright
Electroorganic chemistry 139. Electroreductive decyanation of nitriles and its application to synthesis of α-alkylamines
Shono, Tatsuya,Terauchi, Jun,Kitayama, Kenji,Takeshima, Yo-Ichiro,Masumura, Yoshihiro
, p. 8253 - 8262 (2007/10/02)
Electroreduction of nitriles gave the corresponding decyanated products when Zn was used as the material of cathode in aprotic solvent (DMF or MeCN) containing Et4NOTs as a supporting electrolyte. Alkylation of amines at the α-position was effectively achieved by cyanation of amines at the α-position, and α-alkylation of the resultant α-amino nitriles followed by the electroreductive decyanation.
A NOVEL METHOD FOR COPPER(I)-CATALYZED COUPLING REACTIONS OF TRIFLATES WITH GRIGNARD REAGENTS
Kotsuki, Hiyoshizo,Kadota, Isao,Ochi, Masamitsu
, p. 1281 - 1284 (2007/10/02)
A variety of triflates containing a β-oxygen functionality were efficiently reacted with Grignard reagents in the presence of CuBr to afford the corresponding coupling products.
Stereochemical Assignments of the 7-Phenyl-2-oxabicycloheptanes
Woodyard, James D.,Morris, Paul R.,Hobbs, Gregory D.
, p. 1097 - 1099 (2007/10/02)
A rapid method for making stereochemical assignments based on variant temperature nmr data for the 7-phenyl-2-oxabicycloheptanes is described.
