Search results for " organocatalysi"
showing 9 items of 19 documents
New substituted imidazolidinone as low loading catalyst for α-alkylation of aldehydes
2013
Recyclable Chiral Imidazolidinone Catalyst for α-Alkylation of Aldehydes
2014
Organocatalytic Enantioselective Functionalization of Hydroxyquinolines through an Aza-Friedel-Crafts Alkylation with Isatin-derived Ketimines
2018
[EN] A highly enantioselective addition of hydroxyquinolines to isatin-derived ketimines has been realized using a quinine-derived thiourea organocatalyst. The reaction affords chiral 3-amino-2-oxindoles bearing a quinoline moiety with a quaternary stereocenter in high yields (up to 98%) and excellent enantioselectivities (up to 99%). Moreover, we can extend this methodology for the enantioselective functionalization of 5-hydroxyisoquinoline. This methodology represents, to the best of our knowledge, the first enantioselective addition of hydroxyquinolines to imines.
“Nonsolvent” Applications of Ionic Liquids in Organocatalysis
2012
This chapter is organized in three sections (see Figure 10.1 ): 2. Immobilization of ionic liquids and organocatalysts 2.1 Covalently attached “ ionic liquid ” moieties as supports 2.2 Covalently attached “ ionic liquid ” moieties as linkers 2.3 Covalently attached “ ionic liquid ” moieties as organocatalysts
Supported ionic liquids. New recyclable materials for L-proline-catalyzed aldol reaction
Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction.
2022
A highly stereoselective procedure for the synthesis of spiro-polycyclic oxindoles bearing five contiguous stereogenic centers including two tetrasubstituted carbons has been developed. Under sequential organocatalysis performed by a pyrrolidine-based organocatalyst and DBU, a highly atom-economical Michael–domino Michael/aldol reaction sequence was optimized, yielding variously functionalized spiro-decalin oxindoles with excellent stereoselectivity (>99:1 dr, up to 92% ee). peerReviewed
STABILITY AND ORGANOCATALYTIC EFFICIENCY OF N-HETEROCYCLIC CARBENES ELECTROGENERATED IN ORGANIC SOLVENTS FROM IMIDAZOLIUM IONIC LIQUIDS
2015
The kinetic of degradation of 1-butyl-3-methylimidazole-2-ylidene (selected as model N-heterocyclic carbene - NHC), generated in organic solvents by cathodic reduction of the parent 1-butyl-3- methylimidazolium salts BMIm-X, was studied by a simple voltammetric analysis. The effect of NHC degradation rate on the efficiency of an organocatalyzed reaction (the synthesis of g-butyrolactone from cinnamaldehyde and trifluoromethylacetophenone) was investigated. The nature of the solvent and of the anion X have a remarkable effect on the stability of the NHC, the bis(trifluoromethylsulfonyl) imide anion being the best for a long lasting carbene (while acetonitrile seems to be the worst solvent). …
The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space
2019
Herein, we show that the hexameric resorcinarene capsule C is able to catalyze the formation of bis(heteroaryl)methanes by reaction between pyrroles or indoles and carbonyl compounds (α-ketoesters or aldehydes) in excellent yields and selectivity. Our results suggest that the capsule can play a double catalytic role as a H-bond catalyst, for the initial activation of the carbonyl substrate, and as a Bronsted acid catalyst, for the dehydration of the intermediate alcohol.
Supramolecular Organocatalysis in Water Mediated by Macrocyclic Compounds
2018
In the last decades many efforts have been devoted to design supramolecular organocatalysts able to work in water as the reaction medium. The use of water as solvent provides promising benefits with respect to environmental impact. In this context, macrocyclic compounds played a role of primary importance thanks to their ease of synthesis and their molecular recognition abilities toward the reactants. The aim of this review is to give an overview of the recent advances in the field of supramolecular organocatalysis in water, focusing the attention on calixarene and cyclodextrins derivatives. Calixarenes and cyclodextrins, thanks to their hydrophobic cavities, are able to host selectively th…