First enantioselective one-pot, three-component imino Reformatsky reaction

2006 ◽  
Vol 78 (2) ◽  
pp. 287-291 ◽  
Author(s):  
Pier Giorgio Cozzi ◽  
Eleonora Rivalta

The Reformatsky reaction is the well-recognized carbon-carbon bond-forming reaction of α-halo esters with aldehydes or ketones in the presence of Zn metal to give β-hydroxy esters. Recently, it has been reported that Rh- and Ni-catalyzed Reformatsky reaction, in which R2Zn (R = Me, Et) acts as the Zn source, reacted smoothly with carbonyl compounds and imines. Taking advantage of N-methylephedrine as a cheap and recoverable chiral ligand, we have discovered the first homogeneous enantioselective Ni-catalyzed imino Reformatsky reaction. The process is a one-pot, three-component reaction, in which Me2Zn plays multiple roles as dehydrating agent, reductant, and coordinating metal. Broad scope, high enantiomeric excess, and a simple procedure are adding value to our findings.

2020 ◽  
Vol 7 (1) ◽  
pp. 23-39 ◽  
Author(s):  
Kantharaju Kamanna ◽  
Santosh Y. Khatavi

Multi-Component Reactions (MCRs) have emerged as an excellent tool in organic chemistry for the synthesis of various bioactive molecules. Among these, one-pot MCRs are included, in which organic reactants react with domino in a single-step process. This has become an alternative platform for the organic chemists, because of their simple operation, less purification methods, no side product and faster reaction time. One of the important applications of the MCRs can be drawn in carbon- carbon (C-C) and carbon-heteroatom (C-X; X = N, O, S) bond formation, which is extensively used by the organic chemists to generate bioactive or useful material synthesis. Some of the key carbon- carbon bond forming reactions are Grignard, Wittig, Enolate alkylation, Aldol, Claisen condensation, Michael and more organic reactions. Alternatively, carbon-heteroatoms containing C-N, C-O, and C-S bond are also found more important and present in various heterocyclic compounds, which are of biological, pharmaceutical, and material interest. Thus, there is a clear scope for the discovery and development of cleaner reaction, faster reaction rate, atom economy and efficient one-pot synthesis for sustainable production of diverse and structurally complex organic molecules. Reactions that required hours to run completely in a conventional method can now be carried out within minutes. Thus, the application of microwave (MW) radiation in organic synthesis has become more promising considerable amount in resource-friendly and eco-friendly processes. The technique of microwaveassisted organic synthesis (MAOS) has successfully been employed in various material syntheses, such as transition metal-catalyzed cross-coupling, dipolar cycloaddition reaction, biomolecule synthesis, polymer formation, and the nanoparticle synthesis. The application of the microwave-technique in carbon-carbon and carbon-heteroatom bond formations via MCRs with major reported literature examples are discussed in this review.


2010 ◽  
Vol 352 (17) ◽  
pp. 2881-2886 ◽  
Author(s):  
Alice Devineau ◽  
Guillaume Pousse ◽  
Catherine Taillier ◽  
Jérôme Blanchet ◽  
Jacques Rouden ◽  
...  

RSC Advances ◽  
2018 ◽  
Vol 8 (48) ◽  
pp. 27131-27143 ◽  
Author(s):  
Hajar Hosseini ◽  
Mohammad Bayat

Synthesis of N-amino-3-cyano-2-pyridone derivatives in green solvent with simple procedure and high purity via a one-pot operation.


2013 ◽  
Vol 2013 (16) ◽  
pp. 3337-3346 ◽  
Author(s):  
Noriki Kutsumura ◽  
Yusuke Matsubara ◽  
Kentaro Niwa ◽  
Ai Ito ◽  
Takao Saito

2018 ◽  
Vol 62 (1) ◽  
Author(s):  
Jabbar Khalafy ◽  
Ramin Javahershenas

<p>A green approach for the synthesis of polyfunctionalized pyrrolo[2,3-<em>d</em>]pyrimidine derivatives was successfully achieved by a one-pot, three-component reaction of arylglyoxals, 6-amino-1,3-dimethyluracil and barbituric acid derivatives in the presence of tetra-<em>n</em>-butylammonium bromide (TBAB) (5 mol%) as the catalyst in ethanol at 50 °C. This protocol has many advantages such as high yields (73-95%), green and simple procedure, short reaction times, easy work-up, mild reaction conditions and general applicability.</p>


ChemInform ◽  
2013 ◽  
Vol 44 (45) ◽  
pp. no-no
Author(s):  
Noriki Kutsumura ◽  
Yusuke Matsebara ◽  
Kentaro Niwa ◽  
Ai Ito ◽  
Takao Saito

Synthesis ◽  
2014 ◽  
Vol 47 (01) ◽  
pp. 79-82 ◽  
Author(s):  
John Sorensen ◽  
Miloslav Sailer ◽  
Krystyn Dubicki

2012 ◽  
Vol 9 (4) ◽  
pp. 2037-2043 ◽  
Author(s):  
Abolghasem Davoodnia ◽  
Bahareh Razavi ◽  
Niloofar Tavakoli-Hoseini

Silica gel-supported polyphosphoric acid (PPA-SiO2) was found to be highly efficient, eco-friendly and recyclable heterogeneous catalyst for the synthesis of 2,4,6-triarylpyridines through one-pot three-component reaction of acetophenone, aryl aldehydes, and ammonium acetate under solvent-free conditions. This method has several advantages, such as simple procedure with an easy work-up, short reaction times, and high yields. Furthermore, the catalyst could be recycled after a simple work-up, and used at least three times without substantial reduction in its catalytic activity.


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