Organocatalysis and catalyst aggregation: a study using the asymmetric synthesis of benzofuranones as a test reaction
Literature Information
Luca Massaro, Antonio Puglisi, Lucrezia Angelini, Achille Antenucci, Simone Placidi, Fabio Sciubba, Luciano Galantini, Marco Bella
A common problem encountered in enantioselective organocatalysis is the aggregation of the catalyst, which can result in a relevant decrease of the efficiency and selectivity of the process. In the asymmetric synthesis of chiral benzofuranones, recently reported by us, we noted a remarkable increase of the reaction yield upon the addition of one of the reagents in a portionwise manner rather than in a single addition. We investigated this phenomenon by several experimental techniques such as 1D and 2D NMR experiments, UV-Vis spectroscopy, circular dichroism and dynamic light scattering. In addition, we studied the kinetic profile of this reaction using a simple numerical model and carried out in silico investigations. All these different approaches point to the conclusion that in the reaction medium a supramolecular polymerization/aggregation phenomenon, based on weak interactions, occurs and such a process is promoted by a quinone, which is one of the reagents of the benzofuranone synthesis. The portionwise mode of addition is a known strategy which can improve the performance of many synthetic procedures and this strategy is commonly adopted on account of empirical experience. However, our results provide an explanation, based on a chemical kinetic model, of the reason why the portionwise addition affects in such a dramatic way the yield of the benzofuranone synthesis catalyzed by Cinchona alkaloids.
Related Literature
Real time plasmonic qPCR: how fast is ultra-fast? 30 cycles in 54 seconds
Philip J. R. Roche, Mohamed Najih, Seung S. Lee, Lenore K. Beitel, Matthew L. Carnevale, Andrew G. Kirk
DOI: 10.1039/C7AN00304H
Digital de-waxing on FTIR images
Fabrício Augusto de Lima, Cyril Gobinet, Ganesh Sockalingum, Sérgio Britto Garcia, Michel Manfait, Valérie Untereiner, Olivier Piot, Luciano Bachmann
DOI: 10.1039/C6AN01975G
Benzimidazole-containing aramid nanofiber for naked-eye detection of heavy metal ions
Zheng Cheng, Zhenyuan Bai, Yu Dai, Longbo Luo, Xiangyang Liu
DOI: 10.1039/C8AN01484A
Probing glycosaminoglycan spectral signatures in live cells and their conditioned media by Raman microspectroscopy
H. T. Mohamed
DOI: 10.1039/C6AN01951J
In vivo detection of drug-induced apoptosis in tumors using Raman spectroscopy
Oliver Jonas, Jeon Woong Kang, Surya P. Singh, Alex Lammers, Freddy T. Nguyen, Ramachandra R. Dasari, Peter T. C. So, Robert Langer
DOI: 10.1039/C8AN00913A
Interactions of Hg(ii) with oligonucleotides having thymine–thymine mispairs. Optimization of an impedimetric Hg(ii) sensor
Ajar Kamal, Zhe She, Renu Sharma, Heinz-Bernhard Kraatz
DOI: 10.1039/C7AN00238F
Spectrophotometric analysis at the single-cell level: elucidating dispersity within melanic immortalized cell populations
Gerardo Gutiérrez-Juárez, David Cywiak, Rafael Pérez-Solano, Gary A. Baker
DOI: 10.1039/C6AN02662A
Raman spectroscopy in microsurgery: impact of operating microscope illumination sources on data quality and tissue classification
Joannie Desroches, Audrey Laurence, Michael Pinto, Marie-Andrée Tremblay, Kevin Petrecca, Frédéric Leblond
DOI: 10.1039/C6AN02061E
Sensitive fluorescence detection of heparin based on self-assembly of mesoporous silica nanoparticle–gold nanoclusters with emission enhancement characteristics
Lin Ma, Mengyue Zhang, Aijun Yang, Qin Wang, Fei Qu, Fengli Qu, Rong-Mei Kong
DOI: 10.1039/C8AN01556B
You might also like
What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?
N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...
What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?
When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...
What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?
Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...
What is the market or research trend for oxocopper (CAS: 12053-18-8)?
The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...
What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?
The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...
What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?
2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...
What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?
2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...
How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?
(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...
What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?
3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...
How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?
Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...
Source Journal
Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.














