49835-50-9Relevant academic research and scientific papers
Bis(amino)cyclopropenylidenes as organocatalysts for acyl anion and extended umpolung reactions
Wilde, Myron M. D.,Gravel, Michel
, p. 12651 - 12654 (2013)
Back to BACs: In the pursuit of novel carbene organocatalysts, bis(amino)cyclopropenylidenes (BACs) were explored as alternatives to N-heterocyclic carbenes. They were effective in catalyzing the Stetter reaction, and displayed unique advantages over the
Oxazolium Salts as Organocatalysts for the Umpolung of Aldehydes
Garapati, Venkata Krishna Rao,Gravel, Michel
supporting information, p. 6372 - 6375 (2018/10/15)
Oxazolium salts were successfully employed for the first time as organocatalysts for benzoin, Stetter, and redox esterification reactions. An N-mesityl oxazolium salt catalyzed homobenzoin reaction of aromatic, heteroaromatic, and aliphatic aldehydes delivered α-hydroxy ketones in high yields. This new type of catalyst proved remarkably effective for the Stetter reaction of challenging substrates such as β-alkyl-α,β-unsaturated ketones and electron-rich aromatic aldehydes in comparison to common thiazolium and triazolium salts.
Chemo- and Diastereoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-α-amino Aldehydes
Haghshenas, Pouyan,Gravel, Michel
supporting information, p. 4518 - 4521 (2016/09/28)
N-Boc-α-amino aldehydes are shown to be excellent partners in cross-benzoin reactions with aliphatic or heteroaromatic aldehydes. The chemoselectivity of the reaction and the facial selectivity on the amino aldehyde allow cross-benzoin products to be obtained in good yields and good diastereomeric ratios. The developed method is utilized as the key step in a concise total synthesis of d-arabino-phytosphingosine.
Design, synthesis and anti-mycobacterial activity of 1,2,3,5- tetrasubstituted pyrrolyl-N-acetic acid derivatives
Pagadala, Lakshmi Reddy,Mukkara, Lakshmi Devi,Singireddi, Satyanarayana,Singh, Ashita,Thummaluru, Veera Reddy,Jagarlamudi, Padma Sridevi,Guttala, Raja Sekhar,Perumal, Yogeeswari,Dharmarajan, Sriram,Upadhyayula, Suryanarayana Murty,Ummanni, Ramesh,Basireddy, Venkata Subba Reddy,Ravirala, Narender
, p. 118 - 126 (2014/07/22)
A novel synthesis of highly substituted pyrrole-N-acetic derivatives is described through the coupling of 1,4-diketones with amino acids following Paal-Knorr's approach. These pyrrole-N-acetic acid derivatives are found to exhibit potent anti-mycobacterial activity against Mycobacterium smegmatis and Mycobacterium tuberculosis strain H37Rv. In particular, 5n, 5q & 5r are found to display excellent anti-mycobacterial activity against M. tuberculosis strain H37Rv with MIC values in the range of 2.97 μM. Conversely, these compounds showed low cytotoxicity (selectivity index: >16.83) against HEK-293T cell line.
Synthesis of thermoregulated phase-separable triazolium ionic liquids catalysts and application for Stetter reaction
Yu, Feng-Li,Zhang, Rui-Li,Xie, Cong-Xia,Yu, Shi-Tao
experimental part, p. 9145 - 9150 (2011/01/12)
A series of polyether-substituted triazolium ionic liquids catalysts have been first synthesized for resolving the problem of separation and reuse of Stetter catalysts. The catalysts possess the properties of critical solution temperature (CST) and inverse temperature-dependent solubility in toluene/heptane solvents. Based on these properties, the catalysts can achieve the catalytic process named as thermoregulated phase-separable catalysis (TPSC) with the characteristic of homogeneous reaction at higher temperature and phase-separation at lower temperature. The novel TPSC system has been successfully applied for Stetter reaction of furfural or butanal with ethyl acrylate. The experimental results have showed that the novel catalysts exhibit excellent TPSC with high recycling efficiency.
Michael Additions of Benzoins versus Michael-Stetter Additions of Aldehydes
Castells, Josep,Dunach, Elisabeth,Geijo, Fernando,Lopez-Calahorra, Francisco,Prats, Margarita,et al.
, p. 2291 - 2294 (2007/10/02)
Triethylamine catalyzed Michael additions of benzoines to chalcone can prevail over the expected Michael-Stetter additions when certain thiazolium ion conjugate bases - prepared in situ from the pertinent thiazolium salts and triethylamine - are used as catalysts.
Process for the preparation of ketones
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, (2008/06/13)
The invention concerns a new process for the preparation of ketones; according to this process ketones are prepared from aldehydes and unsaturated compounds in the presence of bases using quaternary ammonium salts as catalysts.
Process for preparing ketones
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, (2008/06/13)
Ketones are prepared by reacting an aromatic or heterocyclic aldehyde in the presence of a cyanide ion with an unsaturated compound having the formula (I): STR1 wherein R1, R2 and R3 are the same or different and are selected from the group of hydrogen, optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic and carboxylic acid ester and R4 is nitrile (CN), --CO--R5 or --CO--OR5 wherein R5 is selected from the group of optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic and heterocyclic and R1 and R2 and/or R1 and R3 and/or R2 and R5 or R3 and R5 together with the carbon atoms to which they are attached as substituents may also form a carbocyclic or heterocyclic ring. Ketones prepared according to the process of the invention have the formula: STR2 wherein R1 ' and R3 ' are identical or different and are selected from the group of hydrogen, lower alkyl having up to 3 C-atoms and optionally substituted phenyl; and R6 ' is optionally substituted phenyl or a pyridyl.
