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Open Chemistry
|
2010
|
vol. 8
|
issue 2
269-272
EN
Sulphonimide based organocatalyst was used to catalyze the aldol reaction in ionic liquid media. On the basis of yield and selectivity the ionic liquid mediated system was found superior in comparison with organic solvents. The added advantages of this ionic liquid mediated organocatalysis are easy recovery of product and the recyclability of the organocatalyst. [...]
EN
Organocatalysis, where organic molecules like α-amino acids, α-hydroxy acids, nucleic acids, carbohydrates are employed to catalyze organic transformations such as the aldol, Mannich and Michael reactions is a rapidly expanding field of organic synthesis. Operational simplicity, ready availability of the catalysts, selectivity, efficiency and low cost make them an attractive alternative to metal-mediated organic transformations. Although organocatalysts have many attractive features, this catalytic system also suffers from often high catalyst loading or poor solubility of the catalyst in organic solvents. Recently, ionic liquids, PEG, montmorillonite clays have been demonstrated to be good supports helping to overcome the limitations mentioned. These supported systems offer accepatble trade-offs in terms of yields and selectivity with the added advantages of recyclability of the catalyst. This review compares various supported and unsupported aminocatalysts mainly focusing on C-C bond forming reactions.
EN
A new organocatalytic system was tested as a promoter for the asymmetric addition of Chan’s diene to aldehydes under solvent-free conditions. This new organocatalyst generated in situ by mixing 1-naphthyl-TADDOL derivative and Emim BF4 was able to give enantioenriched vinylogous aldols and hetero-Diels-Alder cycloadducts. A mechanistic investigation through the detection of nonlinear effects confirmed the involvement of the ionic liquid in the formation of a new catalytic supramolecular species.
EN
Microwave heating was used to synthesise different types of 1, 2, 3 triazolium based ionic liquids (5a-j) with good yield in reduced time. These ionic liquids were further screened as reaction medium for Aldol reaction using two different most promising organocatalysts; proline and proline tetrazole. In both cases, Aldol products were obtained in good yield and selectivity with each ionic liquid. It is important to notify that all the ionic liquids (5a-j) offer 5 times recyclability with our catalytic system (Proline or Proline tetrazole).
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