130284-26-3Relevant academic research and scientific papers
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
NHC-catalyzed ring expansion of oxacycloalkane-2-carboxaldehydes: A versatile synthesis of lactones
Wang, Li,Thai, Karen,Gravel, Michel
supporting information; experimental part, p. 891 - 893 (2009/08/15)
Imidazolinium-derived carbenes catalyze the ring-expansion lactonization of oxacycloalkane-2-carboxaldehydes. A variety of functionalized five-, six-, and seven-membered lactones can be formed efficiently under mild reaction conditions. The success of this new method for the construction of lactones is highly influenced by the electronic nature of the carbene catalyst.
Striking AcOH acceleration in direct intramolecular allylie amination reactions
Nahra, Fady,Liron, Frederic,Prestat, Guillaume,Mealli, Carlo,Messaoudi, Abdelatif,Poli, Giovanni
supporting information; experimental part, p. 11078 - 11082 (2010/04/28)
An experiment was conducted to demonstrate that a strong accelerating effect occurs in direct intramolecular allylic amination when the reaction is conducted in AcOH rather than in CHCl or THF. A round bottom flask under air was charged with N-tosylcarbamate 3a-j, Pd(OAc)2, bis-sulfoxide ligand LL, phenylbenzoquinone and AcOH. The reaction was allowed to stir at 45°C for 24 h. The reaction mixture was hydrolysed and extracted with AcOEt. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Cyclisation of 3a was repeated in CH2Cl 2 and in AcOH by using stoichiometric amounts of Pd(OAc) without benzoquinone. Stoichiometric tests and computational DFT analysis of the palladium reoxidation step provide an overview of the structural and energetic role of acetic acid in increasing the efficacy of the entire catalytic cycle.
Direct catalytic intermolecular α-allylic alkylation of aldehydes by combination of transition-metal and organocatalysis
Ibrahem, Ismail,Cordova, Armando
, p. 1952 - 1956 (2007/10/03)
(Chemical Equation Presented) All in the same pot together: The direct catalytic α-allylic alkylation of aldehydes and cyclic ketones is achieved by using a simple, unprecedented one-pot procedure. Transition-metal and enamine catalysis are combined so that α-allylic alkylated aldehydes and cyclic ketones are formed in high yield with a direct catalytic chemo- and regioselective method.
A novel type of structurally simple nonpeptide inhibitors for α- chymotrypsin. Induced-fit binding of methyl 2-allyl-3-benzene-propanoate to the S2 subsite pocket
Kim, Dong H.,Li, Zhi-Hong,Lee, Soo Suk,Park, Jeong-Il,Chung, Sang J.
, p. 239 - 249 (2007/10/03)
Unexpectedly, methyl and benzyl esters of 2-allyl-3-benzenepropanoic acid were found to be not substrates but potent competitive inhibitors for α-chymotrypsin. The inhibitory property of the structurally simple nonpeptidic compounds is ascribed to their high binding affinity to the enzyme at the S2 rather than S1 subsite pocket. These inhibitors exist in a flexible form in solution, but as they bind to the enzyme bulky contrained conformers present in a minute concentration play an important role, forming tighter enzyme-inhibitor complexes by binding to the large hydrophobic S2 pocket. The contrained conformers are thought to be resulted from intramolecular CH/π interactions between a vinylic proton and the aromatic π-electron cloud in the inhibitor molecules. These compounds constitute novel examples of the induced-fit binding inhibitor of possibly simplest structure.
Amide-based protecting/radical translocating (PRT) groups. Generation of radicals adjacent to carbonyls by 1,5-hydrogen transfer reactions of o-iodoanilides
Curran, Dennis P.,Yu, Hosung,Liu, Hongtao
, p. 7343 - 7366 (2007/10/02)
The o-iodoanilide group is shown to be broadly useful for the generation and subsequent reactions of radicals adjacent to carboxyl groups. The results indicate that this group is one of the best 'protecting/radical translocating' (PRT) groups introduced t
Allyltitanium Triphenoxide: Selective Cleavage of Oxiranes at the More Substituted Carbon Atom
Tanaka, Tetsuaki,Inoue, Tetsuya,Kamei, Katsuhide,Murakami, Kazuo,Iwata, Chuzo
, p. 906 - 908 (2007/10/02)
Allyltitanium triphenoxide was found to be an excellent reagent for regioselective allylation at the more substituted carbon atom of oxiranes.
