76279-30-6Relevant academic research and scientific papers
Deracemization of Racemic Amines to Enantiopure (R)- and (S)-amines by Biocatalytic Cascade Employing ω-Transaminase and Amine Dehydrogenase
Yoon, Sanghan,Patil, Mahesh D.,Sarak, Sharad,Jeon, Hyunwoo,Kim, Geon-Hee,Khobragade, Taresh P.,Sung, Sihyong,Yun, Hyungdon
, p. 1898 - 1902 (2019/02/27)
A one-pot deracemization strategy for α-chiral amines is reported involving an enantioselective deamination to the corresponding ketone followed by a stereoselective amination by enantiocomplementary biocatalysts. Notably, this cascade employing a ω-transaminase and amine dehydrogenase enabled the access to both (R)-and (S)-amine products, just by controlling the directions of the reactions catalyzed by them. A wide range of (R)-and (S)-amines was obtained with excellent conversions (>80 %) and enantiomeric excess (>99 % ee). Finally, preparative scale syntheses led to obtain enantiopure (R)- and (S)-13 with the isolated yields of 53 and 75 %, respectively.
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
Synthesis of enantiopure 6-methoxy-2-naphthylglycolic acid and its application as a resolving agent
Shimada, Takayoshi,Kobayashi, Yuka,Saigo, Kazuhiko
, p. 3807 - 3813 (2007/10/03)
6-Methoxy-2-naphthylglycolic acid (6-MNGA) was designed as a novel acidic resolving agent, on the model of 2-naphthylglycolic acid (2-NGA). Enantiopure 6-MNGA was easily obtained from commercially available 2-bromo-6- methoxynaphthalene through four steps and was found to show a better chiral recognition ability for racemic 1-arylethylamines than the prototype 2-NGA did. The X-ray crystallographic analyses of less-soluble diastereomeric salts revealed that the introduction of a methoxy group at the 6-position of the 2-NGA skeleton made CH/π interaction(s) effective between 6-MNGA molecules and also between the 6-MNGA molecule and the target amine molecule. The methoxy group was also found to contribute to the realization of effective van der Waals interaction. These interactions played important roles for the stabilization of the less-soluble diastereomeric salts to improve the chiral recognition ability of 6-MNGA, compared to that of 2-NGA.
Resolution of methyl-1-phenylethylamines by acidic derivatives of 1-phenylethylamine
Balint, Jozsef,Schindler, Jozsef,Egri, Gabriella,Hanusz, Miklos,Marthi, Katalin,Juvancz, Zoltan,Fogassy, Elemer
, p. 3401 - 3405 (2007/10/03)
Methyl-1-phenylethylamines were resolved by phenylethylamine derivatives formed with a homologous series of dicarboxylic acids. The structure of the 4-methyl-1-phenylethylamine N-(1-phenylethylamine) succinic acid monoamide diastereoisomeric salt was investigated by single crystal X-ray diffraction.
Design of resolving reagents: p-substituted mandelic acids as resolving reagents for 1-arylalkylamines
Kinbara, Kazushi,Sakai, Kenichi,Hashimoto, Yukihiko,Nohira, Hiroyuki,Saigo, Kazuhiko
, p. 1539 - 1542 (2007/10/03)
The resolution of 1-arylalkylamines 2-10 by mandelic acid 1 was studied. It was found that a substituent, which elongated the molecular length of the amines, diminished the resolution efficiency. On the basis of these results, (S)-p-methylmandelic acid (S)-11 and (R)-p-methoxymandelic acid (R)-12 were selected as new resolving reagents for the 1-arylalkylamines; these acids were found to have a higher resolving ability than (R)-1.
Chiral Building Blocks for the Synthesis of Nitrogen-Containing Natural Products, 5. The Enantioselective Synthesis of Optically Active, Benzene Nucleus-Substituted 1-Phenylethylamines from the Corresponding Acetophenones
Bringmann, Gerhard,Geisler, Joerg-Peter,Geuder, Torsten,Kuenkel, Georg,Kinzinger Lioba
, p. 795 - 805 (2007/10/02)
An efficient two-step procedure for the synthesis of enantiomerically pure, benzene nucleus-substituted 1-phenylethylamines 1 is described, with predictable absolute configuration at the stereogenic center: Imine formation from the substituted acetophenones 6 with (S)- or (R)-1-phenylethylamine and subsequent hydrogenation of the resulting Schiff bases 8 over Raney nickel leads to the secondary amines 9 and 10 in high diastereoselectivities.These dibenzylamines are cleaved regioselectively, usually next to the less substituted aromatic ring, giving the desired chiral 1-phenylethylamines 1 in high yields and enantiomeric purities.Scope and limitations of this new and facile approach to the versatile building blocks 1 are reported.
