Reductive Amination of Aliphatic Carbonyls using Low–valent Titanium Reagent: A Convenient Route to free Primary Amines

2002 ◽  
Vol 2002 (6) ◽  
pp. 253-254 ◽  
Author(s):  
Shyam Rele ◽  
Asoke Banerji ◽  
Sanjay Talukdar
Keyword(s):  
Reductive Amination ◽  
Simple Procedure ◽  
Direct Access ◽  
Primary Amines ◽  
Convenient Route ◽  
Low Valent

A simple procedure for reductive amination of aliphatic carbonyls, giving direct access to free primary amines using low–valent titanium (LVT) reagent has been reported.

Primary Amines by Transfer Hydrogenative Reductive Amination of Ketones by Using Cyclometalated IrIIICatalysts

2013 ◽  
Vol 20 (1) ◽  
pp. 245-252 ◽  
Author(s):  
Dinesh Talwar ◽  
Noemí Poyatos Salguero ◽  
Craig M. Robertson ◽  
Jianliang Xiao
Keyword(s):  
Reductive Amination ◽  
Primary Amines

Ambient-Temperature Synthesis of Primary Amines via Reductive Amination of Carbonyl Compounds

ACS Catalysis ◽  
2020 ◽  
Vol 10 (14) ◽  
pp. 7763-7772 ◽  
Author(s):  
Chao Xie ◽  
Jinliang Song ◽  
Manli Hua ◽  
Yue Hu ◽  
Xin Huang ◽  
...  
Keyword(s):  
Ambient Temperature ◽  
Carbonyl Compounds ◽  
Reductive Amination ◽  
Primary Amines ◽  
Temperature Synthesis

Selective Synthesis of Primary Amines by Reductive Amination of Ketones with Ammonia over Supported Pt catalysts

ChemCatChem ◽  
2015 ◽  
Vol 7 (6) ◽  
pp. 921-924 ◽  
Author(s):  
Yoichi Nakamura ◽  
Kenichi Kon ◽  
Abeda Sultana Touchy ◽  
Ken-ichi Shimizu ◽  
Wataru Ueda
Keyword(s):  
Reductive Amination ◽  
Primary Amines ◽  
Selective Synthesis ◽  
Pt Catalysts ◽  
Supported Pt Catalysts

scholarly journals 2,3-Diaminopropanols Obtained from d-Serine as Intermediates in the Synthesis of Protected 2,3-l-Diaminopropanoic Acid (l-Dap) Methyl Esters

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1313
Author(s):  
Andrea Temperini ◽  
Donatella Aiello ◽  
Fabio Mazzotti ◽  
Constantinos M. Athanassopoulos ◽  
Pierantonio De Luca ◽  
...  
Keyword(s):  
Amino Acid ◽  
Reductive Amination ◽  
Methyl Esters ◽  
Primary Amines ◽  
Synthetic Approach ◽  
Protecting Group ◽  
Synthetic Strategy ◽  
Crude Product ◽  
Diaminopropanoic Acid ◽  
Acid Labile

A synthetic strategy for the preparation of two orthogonally protected methyl esters of the non-proteinogenic amino acid 2,3-l-diaminopropanoic acid (l-Dap) was developed. In these structures, the base-labile protecting group 9-fluorenylmethyloxycarbonyl (Fmoc) was paired to the p-toluensulfonyl (tosyl, Ts) or acid-labile tert-butyloxycarbonyl (Boc) moieties. The synthetic approach to protected l-Dap methyl esters uses appropriately masked 2,3-diaminopropanols, which are obtained via reductive amination of an aldehyde prepared from the commercial amino acid Nα-Fmoc-O-tert-butyl-d-serine, used as the starting material. Reductive amination is carried out with primary amines and sulfonamides, and the process is assisted by the Lewis acid Ti(OiPr)4. The required carboxyl group is installed by oxidizing the alcoholic function of 2,3-diaminopropanols bearing the tosyl or benzyl protecting group on the 3-NH2 site. The procedure can easily be applied using the crude product obtained after each step, minimizing the need for chromatographic purifications. Chirality of the carbon atom of the starting d-serine template is preserved throughout all synthetic steps.

scholarly journals Homogeneous cobalt-catalyzed reductive amination for synthesis of functionalized primary amines

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Kathiravan Murugesan ◽  
Zhihong Wei ◽  
Vishwas G. Chandrashekhar ◽  
Helfried Neumann ◽  
Anke Spannenberg ◽  
...  
Keyword(s):  
Density Functional ◽  
Reductive Amination ◽  
Primary Amines ◽  
Metal Catalyst ◽  
Gaseous Ammonia ◽  
Free Energy Surface ◽  
Chemical Research ◽  
Rate Determining Step ◽  
Earth Abundant ◽  
Density Functional Theory Computation

AbstractThe development of earth abundant 3d metal-based catalysts continues to be an important goal of chemical research. In particular, the design of base metal complexes for reductive amination to produce primary amines remains as challenging. Here, we report the combination of cobalt and linear-triphos (bis(2-diphenylphosphinoethyl)phenylphosphine) as the molecularly-defined non-noble metal catalyst for the synthesis of linear and branched benzylic, heterocyclic and aliphatic primary amines from carbonyl compounds, gaseous ammonia and hydrogen in good to excellent yields. Noteworthy, this cobalt catalyst exhibits high selectivity and as a result the -NH2 moiety is introduced in functionalized and structurally diverse molecules. An inner-sphere mechanism on the basis of the mono-cationic [triphos-CoH]+ complex as active catalyst is proposed and supported with density functional theory computation on the doublet state potential free energy surface and H2 metathesis is found as the rate-determining step.

scholarly journals Antimicrobial and antimycobacterial activities of aliphatic amines derived from vanillin

2015 ◽  
Vol 93 (11) ◽  
pp. 1305-1311 ◽  
Author(s):  
Alyssa E. Patterson ◽  
Andrew J. Flewelling ◽  
Trevor N. Clark ◽  
Stephen J. Geier ◽  
Christopher M. Vogels ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Mycobacterium Tuberculosis ◽  
Sodium Borohydride ◽  
Reductive Amination ◽  
Antimycobacterial Activity ◽  
Antibiotic Activity ◽  
Primary Amines ◽  
X Ray Diffraction ◽  
X Ray ◽  
Boron Substitution

Ten lipophilic amines were prepared from the reductive amination of vanillin and the corresponding primary amines using sodium borohydride in methanol. All compounds have been obtained elementally pure and an X-ray diffraction study on the 4-n-butylaniline derivative has confirmed the molecular structure. Whilst the overall antibiotic activity of the derivatives was low, some of these compounds, particularly the boronate ester 2-methoxy-4-((2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)methyl)phenol (7), showed a promising degree of antimycobacterial activity against Mycobacterium tuberculosis H37Ra, where activity seemed to vary by the position of the boron substitution on the aniline ring.

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