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Relevant academic research and scientific papers

Enantiocomplementary synthesis of γ-nitroketones using designed and evolved carboligases

Artificial enzymes created by computational design and directed evolution are versatile biocatalysts whose promiscuous activities represent potentially attractive starting points for divergent evolution in the laboratory. The artificial aldolase RA9S.5-8, for example, exploits amine catalysis to promote mechanistically diverse carboligations. Here we report that RA95.5-8 variants catalyze the asymmetric synthesis of γ-nitroketones via two alternative enantiocomplementary Michael-type reactions: enamine-mediated addition of acetone to nitrostyrenes, and nitroalkane addition to conjugated ketones activated as iminium ions. In addition, a cascade of three aldolasecatalyzed reactions enables one-pot assembly of γ-nitroketones from three simpler building blocks. Together, our results highlight the chemical versatility of artificial aldolases for the practical synthesis of important chiral synthons.

A general, highly enantioselective Michael addition of nitroalkanes to α,β-unsaturated enones catalyzed by 9-amino(9-deoxy)-epi-quinine: a remarkable additive effect

A particularly general protocol for the organocatalytic asymmetric Michael addition of nitroalkanes to α,β-unsaturated enones is reported. The Michael reaction proceeded smoothly and provided the desired adducts in moderate to excellent yields (55–99%) an

Helical-Peptide-Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights

Helical peptide foldamer catalyzed Michael addition reactions of nitroalkane or dialkyl malonate to α,β-unsaturated ketones are reported along with the mechanistic considerations of the enantio-induction. A wide variety of α,β-unsaturated ketones, including β-aryl, β-alkyl enones, and cyclic enones, were found to be catalyzed by the helical peptide to give Michael adducts with high enantioselectivities (up to 99%). On the basis of X-ray crystallographic analysis and depsipeptide study, the amide protons, N(2)-H and N(3)-H, at the N terminus in the α-helical peptide catalyst were crucial for activating Michael donors, while the N-terminal primary amine activated Michael acceptors through the formation of iminium ion intermediates.

(1R,2R)-(+)-(1,2)-DPEN-Bonded Sulfonic Acid Resin: A Trifunctional Heterogeneous Catalyst for Asymmetric Michael Additions of Acetone to Nitroolefins

Based on (1R,2R)-(+)-(1,2)-DPEN skeleton, a series of primary amine-sulfamide bifunctional catalysts were synthesized, which exhibited excellent catalytic performance in the Michael addition of acetone to β-nitrostyrene. Therefore, a trifunctional heterogeneous catalyst was designed and prepared by simple N-sulfonyl reaction of (1R,2R)-(+)-(1,2)-DPEN and sulfonyl chloride resin. It was employed for the aforementioned addition without any additive and satisfactory results (80.5% conversion; 84.3% ee) were obtained. Meanwhile, the structural and textural properties of the catalyst were characterized by infrared spectroscopy (FT-IR), elemental analysis, SEM, and N2 adsorption and desorption experiments. Finally, the generality of the catalyst was investigated.

Highly Enantioselective Michael Addition of Nitroalkanes to Enones and Its Application in Syntheses of (R)-Baclofen and (R)-Phenibut

A highly enantioselective Michael addition of nitroalkanes to α,β-unsaturated ketones was developed. In the presence of a chiral primary amine-thiourea catalyst based on dehydroabietic amine, γ-nitro ketones were obtained with excellent enantioselectiviti

Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines

Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched β-substituted γ-nitroketones. The reaction was performed i

Asymmetric Michael addition of acetone to β-nitrostyrenes catalyzed by novel organocatalysts derived from D-isomannide or Lisoidide

Novel bifunctional organocatalysts were prepared from D-isomannide or L-isoidide in three steps. These catalysts were then evaluated in the asymmetric Michael addition of acetone to trans-.-nitrostyrenes. Although moderate enantioselectivities were observed, this study has highlighted that a simple chiral primary diamine can catalyze this reaction. Furthermore, the reaction was also performed with an isomannide-derived diimine which was transformed in situ into the active catalyst under acidic conditions leading to the best enantioselectivity. ARKAT-USA, Inc.

Asymmetric Michael addition of ketones to nitroolefins: Pyrrolidinyl-oxazole-carboxamides as new efficient organocatalysts

Chiral pyrrolidinyl-oxazole-carboxamides were synthesized and used as efficient new organocatalysts for the asymmetric Michael addition of ketones with nitroalkenes under solvent-free conditions. Gratifyingly, the corresponding Michael adducts were obtain

New simple primary amine-thiourea organocatalysts and their application in asymmetric conjugate addition

A kind of simple primary amine-thiourea organocatalysts was developed. And their application in asymmetric conjugate addition of ketone to nitroalkene was investigated. In the presence of the new primary amine-thiourea, the conjugate addition of ketone to

Enantioselective conjugate addition of both aromatic ketones and acetone to nitroolefins catalyzed by chiral primary amines bearing multiple hydrogen-bonding donors

A new class of chiral primary amine catalysts bearing multiple hydrogen-bonding donors have been designed and synthesized. The newly developed bifunctional organocatalysts efficiently catalyzed not only enantioselective conjugate addition of aromatic keto