136809-07-9Relevant articles and documents
General, green, and scalable synthesis of imines from alcohols and amines by a mild and efficient copper-catalyzed aerobic oxidative reaction in open air at room temperature
Tian, Haiwen,Yu, Xiaochun,Li, Qiang,Wang, Jianxin,Xu, Qing
supporting information, p. 2671 - 2677,7 (2012/12/12)
A general, green, and scalable synthesis of the useful imines and a,b-unsaturated imines is successfully achieved by a low-loading and powerful, mild and efficient copper-catalyzed aerobic oxidative reaction of alcohols and amines in the open air at room temperature under base- and dehydrating reagent-free conditions. This practical reaction can use air as the economic and green oxidant, tolerates a wide range of substrates, can afford high yields of the target imines on a large scale, and produces water as the only by-product, and thus being the best imination method as yet using alcohols and amines directly.
Ruthenium-catalyzed reaction of α,β-unsaturated imines with carbon monoxide and alkenes leading to β,γ-unsaturated γ-butyrolactams: Involvement of direct carbonylation at olefinic C-H bonds as a key step
Chatani, Naoto,Kamitani, Akihito,Murai, Shinji
, p. 7014 - 7018 (2007/10/03)
The reaction of α,β-unsaturated imines with CO and alkenes in the presence of Ru3(CO)12 as a catalyst results in a three-component coupling reaction that gives α,α-disubstituted β,γ-unsaturated γ-butyrolactams. The reaction proceeds via a two-step sequence involving the initial formation of ketone derivatives by catalytic carbonylation at the β-olefinic C-H bonds of α,β-unsaturated imines, followed by the (uncatalyzed) intramolecular nucleophilic attack of the imine nitrogen on the ketonic carbon to generate a tetrahedral intermediate, which then undergoes a 1,2-ethyl migration. The reaction of a cyclic unsaturated imine, derived from the reaction of (1R)-(-)-myrtenal with tertbutylamine, gives a β-aminocyclopentene derivative, which is formed by an aldol-type condensation of the initially formed ketone, indicating the initial formation of ethyl ketone.
PREPARATION OF (E)-α,β-UNSATURATED AROMATIC ALDEHYDES BY HIGH STEREOSELECTIVE OLEFINFORMYLATION.
Gaudemar, Marcel,Bellassoued, Moncef
, p. 349 - 352 (2007/10/02)
Treatment of acetaldehyde N-ter-butylimine by two equivalents of LDA, followed by trimethylsilyl chloride trapping affords the α,α-disilylated imine; the latter reacts with aromatic aldehydes producing α,β-ethylenic aldehydes in excellent yields and with very high stereoselectivity in favour of the E isomer.
PALLADIUM(0)-CATALYZED HYDROXYLAMINATION OF ALLYL ESTERS. SYNTHESIS OF N-ALLYLHYDROXYLAMINES AND SECONDARY ALLYLAMINES
Murahashi, Shun-Ichi,Imada, Yasushi,Taniguchi, Yuki,Kodera, Yoichi
, p. 2973 - 2976 (2007/10/02)
Palladium-catalyzed reaction of allyl esters with hydroxylamines gives N-allylhydroxylamines, which are readily converted into secondary allylamines upon treatment with zinc powder in a dilute HCl solution.
