756474-36-9Relevant academic research and scientific papers
Catalytic Asymmetric Synthesis of N-Chiral Amine Oxides
Bhadra, Sukalyan,Yamamoto, Hisashi
, p. 13043 - 13046 (2016/10/30)
Direct asymmetric synthesis of N-chiral amine oxides was accomplished (up to 91:9 e.r.) by means of a bimetallic titanium catalyst. A hydroxy group situated at the γ-position of the N stereocenter enables the desired N-oxidation through dynamic kinetic resolution of the trivalent amine substrates. The method was further extended to the kinetic resolution of racemic γ-amino alcohols with a preexisting stereocenter, giving an important class of enantioenriched (up to 99.9:0.1 e.r.) building blocks that are otherwise difficult to synthesize.
Ruthenium-catalyzed transfer hydrogenation of nitriles: Reduction and subsequent N-monoalkylation to secondary amines
Werkmeister, Svenja,Bornschein, Christoph,Junge, Kathrin,Beller, Matthias
supporting information, p. 3671 - 3674 (2013/07/19)
The selective synthesis of amines continues to be of importance because of their application in the bulk and fine chemical industries. Herein, domino ruthenium-catalyzed transfer hydrogenation of nitriles with subsequent N-monoalkylation by using alcohols is described. With this novel approach, various nitriles were reductively N-monoalkylated in excellent yields. A simple method for the synthesis of secondary amines starting directly from nitriles by using a ruthenium catalyst is described. With this novel domino system, various nitriles were reduced and subsequently N-monoalkylated in excellent yields (up to 99 %). In addition to isopropanol, other alcohols were also used as a reductant and N-monoalkylation reagent. Copyright
Scope and limitations of the nitro-Mannich reaction for the stereoselective synthesis of 1,2-diamines
Anderson, James C.,Blake, Alexander J.,Howell, Gareth P.,Wilson, Claire
, p. 549 - 555 (2007/10/03)
(Chemical Equation Presented) The acetic acid-promoted addition of lithium nitropropanate and the Lewis acid-catalyzed [Sc-(OTf)3, Cu(OTf) 2, or Ti(OiPr)4] addition of trimethylsilyl nitropropanate to a range of heteroaromatic and simple aliphatic aldimines gave anti-rich (~3-19:1) β-nitroamines in >95% yields as the kinetic products. It was found that a nonpolar N-imine protecting group was essential for reactivity with the o-methoxybenzyl (OMB) group giving better selectivities and yields than p-methoxybenzyl (PMB) or p-methoxyphenyl (PMP) in the Lewis acid-catalyzed addition reactions. Reduction with SmI2, treatment with COCl 2, followed by OMB deprotection gave diastereomerically pure cis-imidazolidinones in 55-79% overall yield from imine. Preliminary results have shown that acetic acid can catalyze the reaction of N-OMB-benzylideneamine with nitropropane, used as solvent, to give the thermodynamically more stable syn-β-nitroamine product.
