53188-66-2Relevant academic research and scientific papers
Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation
Vulovic, Bojan,Trmcic, Milena,Matovic, Radomir,Saicic, Radomir N.
supporting information, p. 9618 - 9621 (2019/12/24)
Unsaturated oxyallyl cations with a suitably positioned alkene bond undergo 5-exo-cyclization with the formation of vinylcyclopentane derivatives. Alkyne analogues provide allenes. The reaction proceeds with a moderate to excellent level of stereoselectiv
Aminomethylation reaction of Ortho -pyridyl C-H bonds catalyzed by group 3 metal triamido complexes
Nagae, Haruki,Shibata, Yu,Tsurugi, Hayato,Mashima, Kazushi
supporting information, p. 640 - 643 (2015/01/30)
Tris[N,N-bis(trimethylsilyl)amido] complexes of group 3 metals, especially yttrium and gadolinium, served as catalysts for ortho-C-H bond addition of pyridine derivatives and N-heteroaromatics into the C=N double bond of nonactivated imines to afford the corresponding aminomethylated products. Addition of catalytic amounts of secondary amines, such as dibenzylamine, dramatically improved the catalytic activity through the formation of a mixed ligated complex such as [(Me3Si)2N]2Y(NBn2)(THF) (4). Furthermore, kinetic studies using the isolated complex 4 provided a plausible reaction mechanism by which coordination of two pyridine derivatives afforded a penta-coordinated species as a key step.
PROCESS FOR PREPARING UNSYMMETRIC SECONDARY TERT-BUTYLAMINES IN THE LIQUID PHASE
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Page/Page column 6, (2011/10/19)
The present application relates to a process for preparing unsymmetric secondary tert-butylamines which, as well as the tert-butyl radical, also comprise an alkyl, cycloalkyl or benzyl radical. They are prepared by reacting corresponding aldehydes with tert-butylamine and hydrogen in the presence of hydrogenation catalysts (reductive amination) in the liquid phase.
Transfer hydrogenation of imines with ammonia-borane: A concerted double-hydrogen-transfer reaction
Yang, Xianghua,Zhao, Lili,Fox, Thomas,Wang, Zhi-Xiang,Berke, Heinz
supporting information; experimental part, p. 2058 - 2062 (2010/06/20)
(Chemical Equation Presented) Direct transfer hydrogenation of imines was observed with ammonia-borane, which proceeded under mild conditions without the help of a catalyst. The results of deuterium kinetic isotope effects, Hammett correlations, and DFT calculations all support a concerted double-hydrogen- transfer mechanism (see scheme).
A stannous chloride-induced deacetalisation-cyclisation process to prepare the ABC ring system of 'upenamide
Reid, Mark,Taylor, Richard J. K.
, p. 4181 - 4183 (2007/10/03)
A stannous chloride-induced deacetalisation-cyclisation approach to the ABC core of the macrocyclic alkaloid, 'upenamide is reported. The use of a substituted β-lactone to prepare a C-2 substituted 'upenamide analogue is also disclosed.
Metalation of diazines XVII. Very hindered bases as new metalating agents, improvement of regioselectivity for the metalation of 3-chloro-6-methoxypyridazine
Mojovic, Ljubica,Turck, Alain,Ple, Nelly,Dorsy, Muriel,Ndzi, Bruno,Queguiner, Guy
, p. 10417 - 10426 (2007/10/03)
The different factors governing the regioselectivity of the metalation of 3-chloro-6-methoxypyridazine with alkylamides were studied. Very hindered bases were used as new metalating agents and a very good regioselectivity was obtained.
Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
Abdel-Magid, Ahmed F.,Carson, Kenneth G.,Harris, Bruce D.,Maryanoff, Cynthia A.,Shah, Rekha D.
, p. 3849 - 3862 (2007/10/03)
Sodium triacetoxyborohydride is presented as a general reducing agent for the reductive amination of aldehydes and ketones. Procedures for using this mild and selective reagent have been developed for a wide variety of substrates. The scope of the reaction includes aliphatic acyclic and cyclic ketones, aliphatic and aromatic aldehydes, and primary and secondary amines including a variety of weakly basic and nonbasic amines. Limitations include reactions with aromatic and unsaturated ketones and some sterically hindered ketones and amines. 1,2-Dichloroethane (DCE) is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran (THF) and occasionally in acetonitrile. Acetic acid may be used as catalyst with ketone reactions, but it is generally not needed with aldehydes. The procedure is carried out effectively in the presence of acid sensitive functional groups such as acetals and ketals; it can also be carried out in the presence of reducible functional groups such as C-C multiple bonds and cyano and nitro groups. Reactions are generally faster in DCE than in THF, and in both solvents, reactions are faster in the presence of AcOH. In comparison with other reductive amination procedures such as NaBH3CN/MeOH, borane-pyridine, and catalytic hydrogenation, NaBH(OAc)3 gave consistently higher yields and fewer side products. In the reductive amination of some aldehydes with primary amines where dialkylation is a problem we adopted a stepwise procedure involving imine formation in MeOH followed by reduction with NaBH4.
ASYMMETRIZATION OF MESO-CYCLIC KETONES USING HOMOCHIRAL ACETAL TEMPLATES
Naruse, Yuji,Yamamoto, Hisashi
, p. 6021 - 6030 (2007/10/02)
Employing the homochiral acetal template, asymmetrization of meso-substituted cyclohexanones is explored.By the use of optically-active 2,4-pentanediol as a chiral protecting group, highly diastereoselective acetal cleavage is achieved when treated with organoaluminum reagent.Dialkylaluminum amides are also effective reagents for this reaction.
