130562-17-3Relevant academic research and scientific papers
Step-efficient access to chiral primary amines
Nugent, Thomas C.,Marinova, Sofiya M.
, p. 153 - 166 (2013/02/25)
Routes to enantioenriched amines are outlined that employ reductive amination and carbanion addition methods. The strategies require either one or two reaction steps from prochiral carbonyl compounds for the synthesis of the corresponding chiral primary amines. Georg Thieme Verlag Stuttgart New York.
Sequential reductive amination-hydrogenolysis: A one-pot synthesis of challenging chiral primary amines
Nugent, Thomas C.,Negru, Daniela E.,El-Shazly, Mohamed,Hu, Dan,Sadiq, Abdul,Bibi, Ahtaram,Umar, M. Naveed
, p. 2085 - 2092 (2011/10/19)
Difficult-to-access chiral primary amines were formed in good to high yield and ee using a rare example of a one-pot synthesis from prochiral ketones (sequential reductive amination-hydrogenloysis). As a highlight we also demonstrate a one-pot reductive amination-hydrogenolysis-reductive amination (five reactions) of ortho-methoxyacetophenone resulting in the chiral diamine 1-(2-methoxyphenyl)ethyl-(2-pyridylmethyl)-amine (4) (58% overall yield, >99% ee), a new organocatalyst for aqueous enantioselective aldol reactions. Copyright
Practical synthesis of optically active fluorine-substituted α-phenylethylamines by retardation of hydrogenolytic cleavage at benzylic position
Kanai, Masatomi,Yasumoto, Manabu,Kuriyama, Yokusu,Inomiya, Kenjin,Katsuhara, Yutaka,Higashiyama, Kimio,Ishii, Akihiro
, p. 1424 - 1425 (2007/10/03)
High regioselectivity in hydrogenolysis of bis(α-methylbenzyl)amines having a fluorine atom on aromatic ring results from retardation of hydrogenolytic cleavage at benzylic position of fluorine-substituted aromatic ring.
A FACILE METHOD FOR THE ASYMMETRIC SYNTHESIS OF ENANTIOMERICALLY PURE 1-(2-FLUOROPHENYL)ETHYLAMINE
Bringmann, G.,Geisler, J.-P.
, p. 67 - 73 (2007/10/02)
A simple, two-step procedure for the synthesis of optically active (S)-1-(2-fluorophenyl)ethylamine (1) is described.Starting from commercially available 2-fluoroacetophenone (2), imination with (S)-1-phenylethylamine (3), followed by stereoselective hydrogenation over Raney-nickel gives the secondary amine 5a.Subsequent regioselective hydrogenolytic cleavage of homogenous 5a yields enantiomerically pure 1.
