This paper describes step-economic iodine-mediated construction of functionalized arylazopyrazoles in the presence of catalytic AgNO3 starting from simple β-ketoesters and two equivalents of arylhydrazines. This cascade reaction includes in situα-iodination of β-ketoesters, pyrazol-3-one formation, substitution with a nitrogen nucleophile, and oxidation/aromatization.

The first example of catalytic asymmetric 1,2-addition of arylboronic acids to heteroaryl α-ketoesters has been developed for the highly efficient and enantioselective synthesis of quaternary carbon-containing heteroaromatic α-hydroxy esters. The reaction works well with a variety of α-ketoesters including 3-indoleglyoxylates, 3-benzofuranglyoxylates and 3-benzothiopheneglyoxylates under very m...

Asymmetric Michael addition of 1-acetylindolin-3-ones to β,γ-unsaturated α-ketoesters was investigated for the synthesis of chiral indolin-3-ones with two adjacent tertiary stereogenic centers. Under the catalysis of a chiral bifunctional squaramide derived from l-tert-leucine, a wide range of 1-acetylindolin-3-ones and β,γ-unsaturated α-ketoesters were well-tolerated in this transformation to ...

Reactions of 2-amino-aryl alcohols with beta-ketoesters catalyzed by a catalytic amount of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation-cyclization, 2-nitrophenyl propargyl alcohols with beta-ketoesters catalyzed by FeCl3 and SnCl2 also produce the 4-alkyne-3-quinolinecarboxyl...

2-Amino-4-benzoyl-1-arylpyrrole-3-carbonitriles react with arylidene malonodinitriles, β-ketoesters and βdiketones to afford pyrrolo[2,3-b]pyridine derivatives.

Sequential Wolff rearrangement of α-diazo-β-ketoesters followed by trapping of the ketene intermediates with enol ethers generated a variety of γ,δ-unsaturated β-ketoesters. This method involves a novel thermal cascade reaction and allows the synthesis of γ,δ-unsaturated β-ketoesters with trans-stereochemistry under catalyst-free conditions. The synthesized compounds were further transformed in...

An organocatalysed and chemoselective one-pot oxa-Michael-cyclocondensation reaction of N-BocNHOH to unsaturated α-ketoesters is reported which affords an original entry to enantioenriched 3-isoxazoline carboxylate derivatives as biorelevant heterocyclic frameworks.

This study presents the bioreduction of six β-ketoesters by whole cells of Kluyveromyces marxianus and molecular investigation of a series of 13 β-ketoesters by hologram quantitative structure-activity relationship (HQSAR) in order to relate with conversion and enantiomeric excess of β-stereogenic-hydroxyesters obtained by the same methodology. Four of these were obtained as (R)-configuration a...