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Upstream product

• 186581-53-3 diazomethane 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 75-52-5 nitromethane 

Relevant academic research and scientific papers

Anti-Selective Catalytic Asymmetric Nitroaldol Reaction of α-Keto Esters: Intriguing Solvent Effect, Flow Reaction, and Synthesis of Active Pharmaceutical Ingredients

A rare-earth metal/alkali metal bimetallic catalyst proved particularly effective for enantioselectively coupling nitroalkanes and α-keto esters in an anti-selective manner to afford synthetically versatile, densely functionalized, and optically active α-nitro tertiary alcohols. A chiral diamide ligand captured two distinct metal cations, giving rise to a catalytically competent solid-phase heterobimetallic catalyst by simple mixing via self-assembly. The advantage of the solid-phase asymmetric catalyst was realized by successful application to the enantio- and diastereoselective reaction in a continuous-flow platform. The use of closely related solvents in terms of structures and polarity parameters, THF and its methylated congener 2-Me-THF, had an unexpectedly large solvent effect both on the reaction rate and the stereoselectivity. The nitroaldol products share a privileged unit for active pharmaceutical ingredients, as demonstrated by the streamlined enantioselective synthesis of the marketed antifungal agents efinaconazole and albaconazole.

Catalytic enantioselective Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine: N -oxides

A pre-prepared Ni-PyBisulidine complex has been developed for the catalytic asymmetric Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides. The corresponding β-nitro-α-hydroxy esters were obtained in good to excellent yields (up t

Synthesis of N,N′-Dialkylated Cyclohexane-1,2-diamines and Their Application as Asymmetric Ligands and Organocatalysts for the Synthesis of Alcohols

A series of N,N′-dialkylated derivatives of (1R,2R)-cyclohexane-1,2-diamine were synthesized, and a new approach to the one-pot preparation of this type of amine was demonstrated. The prepared diamines were used as organocatalysts for the two-step synthesis of α-hydroxy γ-keto esters from arenes, chlorooxoacetates, and ketones; they were also used as chiral ligands for Meervein-Ponndorf-Verley reductions and Henry reactions.

The construction of quaternary stereocenters by the Henry reaction: Circumventing the usual reactivity of substituted glyoxals

The enantioselective Henry reaction between alkyl- and arylglyoxal hydrates and nitromethane catalyzed by CuII-iminopyridine complexes takes place regioselectively on the ketone carbonyl group to give chiral tertiary nitroaldols with high functional group density and enantiomeric excesses of up to 96 %. Both aromatic and aliphatic glyoxals are suitable substrates for this reaction.

Enantioselective nitroaldol reaction of α-keto esters catalyzed by a copper(II)-bisoxazolidine complex

A wide range of aliphatic and aromatic -keto esters has been transformed to α-hydroxy-β-nitro esters via the Cu(II)-bisoxa-zolidine-catalyzed Henry reaction. In the presence of 10 mol% of the chiral catalyst, nitroaldol products were obtained in up to 95% yield and 76% ee.