2-Azanorbornyl-derived amino alcohols were prepared and evaluated as ligands in the Ru(II)-catalyzed asymmetric transfer hydrogenation of aromatic ketones. To improve selectivity and rate, the structure of the ligand was optimized. Acetophenone was reduced using 0.5 mol % catalyst in 40 min in 94% ee. This system was also able to reduce a wide range of aromatic ketones to the corresponding alco...

Catalytic chemoselective reactions of innately less reactive functionalities over more are described. A cooperative catalyst comprising a soft Lewis acid/hard Brønsted base enabled activation hydroxyl group an amino group, allowing for nucleophilic addition to electron-deficient olefins. The reaction could be applicable variety alcohols, including pharmaceuticals, without requiring tedious prot...

A three-component 1,2-aminoarylation of vinyl ethers, enamides, ene-carbamates and thioethers by synergistic photoredox nickel catalysis is reported. 2,2,2-Trifluoroethoxy carbonyl protected α-amino-oxy acids are used as amidyl radical precursors. anti-Markovnikov addition the to alkene Ni-mediated radical/transition metal cross over lead corresponding product. The cascade, which can be conduct...

The oxidation of alcohols to the corresponding carbonyl or carboxyl compounds represents a convenient strategy for the selective introduction of electrophilic carbon centres into carbohydrate-based starting materials. The O₂-dependent oxidation of prim-alcohols by flavin-containing alcohol oxidases often yields mixtures of aldehyde and carboxylic acid, which is due to "over-oxidation" of the al...

Ehrlich and demethiolation pathways as two competing branches converted amino acid into alcohols. Controlling both pathways offers considerable potential for industrial applications including alcohols overproduction, flavor-quality control and developing new flavors. While how to regulate ehrlich and demethiolation pathways is still not applicable. Taking the conversion of methionine into methi...

Nature uses a limited set of metabolites to perform all of the biochemical reactions. To increase the metabolic capabilities of biological systems, we have expanded the natural metabolic network, using a nonnatural metabolic engineering approach. The branched-chain amino acid pathways are extended to produce abiotic longer chain keto acids and alcohols by engineering the chain elongation activi...

Bis(oxazolinyl)phenylrhodium(III) aqua complexes, (Phebox)RhX₂(H₂O) [X = Cl, Br], were found to be efficient Lewis acid catalysts for the enantioselective addition of allyl- and methallyltributyltin reagents to amino aldehydes. The reactions proceed smoothly in the presence of 5-10 mol % of (Phebox)RhX₂(H₂O) complex at ambient temperature to give the corresponding amino alcohols with modest to ...

We report the first one-pot reductive homocoupling reaction of secondary amides and cross-coupling reaction of secondary amides with ketones to give secondary vicinal diamines and amino alcohols. This method relies on the direct generation of α-amino carbon radicals from secondary amides by activation with trifluoromethanesulfonic anhydride, partial reduction with triethylsilane and samarium di...

Anhydrous Cu(OAc)2 mediated efficient protocol has been developed in the area of C-O coupling from potassium aryltrifluoroborates and aliphatic amino alcohols such as β-hydroxy, γ-hydroxy, and δ-hydroxy amines. The scope of this transformation focuses on direct O-arylation and Ostyrylation. The reaction vial loaded with reactants under argon atmosphere is microwaved at 140°C for 30 min to furni...

Here we report that, unlike other ketones, 1-indanone and acetophenone derived enolates undergo Mannich-type addition reactions with N-tert-butanesulfinyl ketimines with excellent yields (up to 98%) and diastereoselectivity (>99/1). The resulting compounds represent a new type of biologically relevant β-aminoketone derivative bearing quaternary stereogenic carbon, which could be further convert...