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Relevant academic research and scientific papers

Design, synthesis and catalytic property of L-proline derivatives as organocatalysts for direct aldol reaction

A series of chiral prolinamide compounds with pyridine-2, 6-dicarboxylic acid moieties derived from L-proline have been designed and synthesized, their catalytic properties for direct asymmetric aldol reactions were also studied in this article. These catalysts gave the aldol product in high yield (87%) and high enantioselectivity, up to 85%, of the anti-structure at room temperature but gave disappointing results at a lower temperature or when additive was added. Conditions, including solvents, temperature and additives were screened for the reactions. Moreover, the influence of presence of water on yield and stereoselectivity was also discussed. Copyright

Aqua-organocatalyzed direct asymmetric aldol reaction with acyclic amino acids and organic bases with control of diastereo- and enantioselectivity

An effective aqua-organocatalytic direct aldol reaction is described. Aromatic amino acids can be a bifunctional catalyst system, which demonstrate excellent reactivity, diastereoselectivity, and enantioselectivity (up to 96% ee) in water without the addi

Supported l-proline on zirconium phosphates methyl and/or phenyl phosphonates as heterogeneous organocatalysts for direct asymmetric aldol addition

Zirconium phosphates methyl and/or phenyl phosphonates-supported l-proline have been prepared as amorphous solids by precipitation of (4R)-4-(phosphonooxy) -l-proline, methyl and/or phenyl phosphonic acid with ZrOCl2. The supported l-proline ca

Nanosheet-enhanced asymmetric induction of chiral α-amino acids in catalytic aldol reaction

An efficient ligand design strategy towards boosting asymmetric induction was proposed, which simply employed inorganic nanosheets to modify α-amino acids and has been demonstrated to be effective in vanadium-catalyzed epoxidation of allylic alcohols. Here, the strategy was first extended to zinc-catalyzed asymmetric aldol reaction, a versatile bottom-up route to make complex functional compounds. Zinc, the second-most abundant transition metal in humans, is an environment-friendly catalytic center. The strategy was then further proved valid for organocatalyzed metal-free asymmetric catalysis, that is, α-amino acid catalyzed asymmetric aldol reaction. Visible improvement of enantioselectivity was experimentally achieved irrespective of whether the nanosheet-attached α-amino acids were applied as chiral ligands together with catalytic ZnII centers or as chiral catalysts alone. The layered double hydroxide nanosheet was clearly found by theoretical calculations to boost ee through both steric and H-bonding effects; this resembles the role of a huge and rigid substituent. Sheeting the system: The chiral induction of α-amino acids was found to be significantly improved when attached to rigid layered double hydroxide nanosheets (see scheme), irrespective of whether they were applied as chiral ligands for ZnII centers or as asymmetric catalysts alone in the direct aldol reaction. Copyright

Chemoenzymatic synthesis of optically active 2-(2′- or 4′-substituted-1H-imidazol-1-yl)cycloalkanols: Chiral additives for (l)-proline

Enantiopure substituted imidazoles obtained by enzymatic kinetic resolution can be promising candidates as co-catalysts for aldol reactions catalysed by (l)-proline. These additives seem to form supramolecular complexes with the catalyst through the forma

L-proline functionalized pillar-layered MOF as a heterogeneous catalyst for aldol addition reaction

A pillar-layered proline-functionalized MOF, [Zn2(2,6-ndc)2(bpb-NHPro)] (I), was synthesized through a solvothermal reaction of Zn(NO3)2 with 1-L-Pyrrolidine-2-carboxamide-2, 5-bis(4-pyridyl)benzene (bpb-NHPro) and 2,6-naphthalenedicarboxylic acid (H2ndc) in N,N-diethyl formamide (DEF). The aldol addition between cyclopentanone and 4-nitrobenzaldehyde was selected as a model reaction for the estimation of the catalytic performance of I, which showed reversed diastereoselectivity, preferring syn-adduct, in contrast to homogeneous catalysis with excellent yield up to 98% and diastereomeric excess up to 98:2 (syn:anti).

A supramolecular hydrogel as a reusable heterogeneous catalyst for the direct aldol reaction

An l-proline based supramolecular hydrogel is used as an efficient heterogeneous organocatalyst for the direct aldol reaction with high stereoselectivity (up to 90% ee) and recyclability (up to 3 runs). The reversible nature of this self-assembled supramo

Chiral metal-organic frameworks bearing free carboxylic acids for organocatalyst encapsulation

Two chiral carboxylic acid functionalized microand mesoporous metal-organic frameworks (MOFs) are constructed by the stepwise assembly of triple-stranded hepta-metallic helicates with six carboxylic acid groups. The meso-porous MOF with permanent porosity

Positive Effect of Water in Asymmetric Direct Aldol Reactions with Primary Amine Organocatalyst: Experimental and Computational Studies

The origin of higher reactivity in water-accelerated asymmetric aldol reactions with our designed primary amine organocatalyst was elucidated by both computational and experimental methods. As suggested by the calculated transition-state structures for wa

"Click" post-synthetic modification of metal-organic frameworks for asymmetric aldol catalysis

The reaction of dimethyl 5-(prop-2-ynyloxy)isophthalic acid, meso-alpha, and beta-di (4-pyridyl) glycol with ZnCl2 in a methanol aqueous solution affords MOF Zn-DPPG. The enantiomeric Zn-Fun1 and Zn-Fun2 were obtained through a strategy of in s