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Relevant academic research and scientific papers

Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles

A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).

Light-Enabled Enantiodivergence: Stereospecific Reduction of Activated Alkenes Using a Single Organocatalyst Enantiomer

Light-enabled enantiodivergence is demonstrated in which the alkene substrate configuration is manipulated (E → Z) prior to organocatalytic reduction with a chiral thiourea and Hantzsch ester. This allows stereodivergent reduction to be regulated at the substrate level with high fidelity and mitigates the need for a second, enantiomeric catalyst (up to 93:07 and 95:5 er). The synthetic utility of this strategy has been demonstrated in the synthesis of the weight-loss drug (R)-Lorcaserin (Belviq) and a potent AMPA modulator.

Substrate Scope Evaluation of the Enantioselective Reduction of β-Alkyl-β-arylnitroalkenes by Old Yellow Enzymes 1-3 for Organic Synthesis Applications

The substrate scope of the old yellow enzyme catalyzed reduction of β-alkyl-β-arylnitroalkenes is investigated. Compounds bearing either alkyl chains of increasing length at the carbon atom in position β to the nitro group or different substituents on the aromatic ring are prepared and submitted to bioreduction, to define the synthetic potential of this enantioselective reaction in the preparation of chiral fine chemicals. The versatility of the resulting nitroalkanes as chiral building blocks is shown by reducing the nitro group into a primary amine and by converting it into a carboxylic acid moiety by Meyer reaction. An "explosion" of chiral products can be observed by combining the highly enantioselective ene-reductase-mediated reduction of nitroalkenes with the chemical versatility of the nitro group.

Metal-Templated Design: Enantioselective Hydrogen-Bond-Driven Catalysis Requiring only Parts-per-Million Catalyst Loading

Based on a metal-templated approach using a rigid and globular structural scaffold in the form of a bis-cyclometalated octahedral iridium complex, an exceptionally active hydrogen-bond-mediated asymmetric catalyst was developed and its mode of action inve

A novel chiral bisphosphine-thiourea ligand for asymmetric hydrogenation of β,β-disubstituted nitroalkenes

A novel chiral bisphosphine-thiourea ligand was developed and applied in the highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes (up to 99% yield and 99% ee). With low catalytic loading (0.25 mol %), 98% ee and 98% conversion were obta

Highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes

Building the building blocks: A highly enantioselective hydrogenation of ?-aryl-?-alkyl disubstituted nitroalkenes 1 has been developed. This method results in enantiomerically pure nitroalkanes 2, which are versatile precursors for chemical synthesis.

Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins

This paper focuses on readily accessible thiourea hydrogen bond catalysts derived from amino acids, whose steric and electronic features are modulated by their degree of substitution at the carbinol carbon center. These catalysts were applied in the asymmetric transfer hydrogenation of nitroolefins furnishing the chiral products in up to 99% yield and 86% enantiomeric excess. The proposed catalyst's mode of action is supported by mechanistic investigations.

Stereochemical analysis of the enzymic reduction of the double bond of α- and β-substituted nitrostyrenes and α-ethoxycinnamaldehyde through deuterium labelling experiments

2H NMR studies and comparison with authentic labelled reference compounds prepared from the (Z)-acetamidocinnamic acid 10 and from (Z)-2-ethoxy-3-(4-methoxyphenyl) prop-2-en-1-ol (14), respectively, by catalytic syn reduction with deuterium gas

Chemoselective and enantioselective transfer hydrogenation of Β, Β-disubstituted nitroalkenes catalyzed by a water-insoluble chiral diaminerhodium complex in water

Asymmetric transfer hydrogenation of Β, Β-disubstituted nitroalkenes catalyzed by a chiral diaminerhodium complex in combination with HCO2NaHCO2H as a hydrogen source in water was successfully realized with high reactivity, excellent chemoselectivity and good enantioselectivity. The metal precursor and pH value of the aqueous solution have a large influence on the reactivity and chemoselectivity. The substituents on the benzene rings and the sulfonyl groups of TsDPEN have significant effects on the enantioselectivity. This catalytic asymmetric transformation is one of the most practical pathways to obtain optically active nitroalkanes.

Transfer hydrogenation in water: Enantioselective, catalytic reduction of (E)-β,β-disubstituted nitroalkenes

A mild catalytic asymmetric transfer hydrogenation of β,β- disubstituted nitroalkenes Is reported. Formic acid Is used as a reductant in combination with an Ir catalyst. The reaction Is conducted in water at low pH and open to air to give adducts In prepa