14 research outputs found
rac-2,2âČ-Bipiperidine-1,1âČ-diium dibromide
In the title compound, C10H22N2
2+·2Brâ, a precursor in the synthesis of organocatalysts, the bipiperidinium ion is located on a twofold rotation axis which passes through the mid-point of the central CâC bond. The piperidinium ring adopts a chair conformation. In the crystal, the cations are linked together by Brâ ions through NâHâŻBr hydrogen bonds, forming layers parallel to the ab plane
Protocol for the preparation of primary amine-containing catalysts on the resin
Summary: In light of escalating sustainability concerns, addressing catalyst usage and waste production challenges becomes crucial. Here, we introduce a robust protocol for crafting recyclable polystyrene-supported primary amines, providing a promising solution via heterogeneous catalysis. The protocol details immobilization onto insoluble resins through ester, ether, or amide bonds, facilitating the synthesis of heterogeneous catalysts with diverse organic components.For complete details on the use and execution of this protocol, please refer to Kanger et al.1 : Publisherâs note: Undertaking any experimental protocol requires adherence to local institutional guidelines for laboratory safety and ethics
Bimorpholines as Alternative Organocatalysts in Asymmetric Aldol Reactions
Asymmetric organocatalytic aldol condensation is discussed on the basis of intramolecular and inter-molecular reactions. In addition to the widely used proline and its derivatives an application of the new type of the organocatalyst â bimorpholines in the above-mentioned reactions
is described. The new catalyst has a unique C2-symmetric skeleton with four acceptor sites that makes it stereoselective and efficient. Small changes in the structure of the catalyst lead to a remarkable loss of selectivity
Primary amines as heterogeneous catalysts in an enantioselective [2,3]-Wittig rearrangement reaction
Summary: A series of heterogeneous catalysts anchored to different polystyrene-based supports has been prepared and applied in an asymmetric [2,3]-Wittig rearrangement reaction of cyclohexanone derivatives. Among them, primary amino acid-derived (aminomethylated)polystyrene-supported catalysts showed excellent reactivity leading to the formation of rearranged products in good enantioselectivities of both diastereomers. Reusability issues connected to the deactivation of the catalyst were proved to be dependent on the end-capping strategy chosen for the blocking of the unreacted active sites of the resin. This issue of end-capping has not previously been in focus. Using bulkier pivaloyl end-capping moiety, we were able to recycle the catalyst in six consecutive cycles with only marginal deceleration of the reaction. Moreover, the epimerization of the product that occurred while conducting a rearrangement reaction in the presence of a homogeneous catalyst was almost fully eliminated by switching the catalytic system to heterogeneous
ChemInform Abstract: Bimorpholines as Alternative Organocatalysts in Asymmetric Aldol Reactions
Asymmetric organocatalytic aldol condensation is discussed on the basis of intramolecular and inter-molecular reactions. In addition to the widely used proline and its derivatives an application of the new type of the organocatalyst â bimorpholines in the above-mentioned reactions
is described. The new catalyst has a unique C2-symmetric skeleton with four acceptor sites that makes it stereoselective and efficient. Small changes in the structure of the catalyst lead to a remarkable loss of selectivity
Asymmetric Organocatalytic Michael AdditionâCyclisation Cascade of Cyclopentane-1,2-dione with Alkylidene Malononitriles
Synthesis and use of 3,3'-bimorpholine derivatives in asymmetric Michael addition and intramolecular aldol reaction
3,3'-Bimorpholine derivatives as a new class of organocatalysts for asymmetric michael addition
New N-alkyl-3,3'-bimorpholine derivatives (iPBM) were revealed to be efficient organocatalysts for the asymmetric direct Michael addition of aldehydes to nitroolefins and a vinyl sulfone. In these transformations using iPBM, 1,4-adducts were afforded in high yields, with good to high levels of diastereo- and enantioselectivity. The stereochemical outcome of the reaction could be explained by an acyclic synclinal model