54568-58-0Relevant academic research and scientific papers
Stereodivergent Nucleophilic Additions to Racemic β-Oxo Acid Derivatives: Fast Addition Outcompetes Stereoconvergence in the Archetypal Configurationally Unstable Electrophile
Crawford, Evan T.,De Jesús Cruz, Pedro,Johnson, Jeffrey S.,Liu, Shubin
supporting information, p. 16264 - 16273 (2021/10/21)
Additions of carbon nucleophiles to racemic α-stereogenic β-oxo acid derivatives that deliver enantiomerically enriched tertiary alcohols are valuable, but uncommon. This article describes stereodivergent Cu-catalyzed borylative cyclizations of racemic β-oxo acid derivatives bearing tethered pro-nucleophilic olefins to deliver highly functionalized cyclopentanols containing four contiguous stereogenic centers. The reported protocol is applicable to a range of β-oxo acid derivatives, and the diastereomeric products are readily isolable by typical chromatographic techniques. α-Stereogenic-β-keto esters are typically thought to have extreme or spontaneous configurational fragility, but mechanistic studies for this system reveal an unusual scenario wherein productive catalysis occurs on the same time scale as background substrate racemization and completely outcompetes on-cycle epimerization, even under the basic conditions of the reaction.
An efficient and rapid synthesis of β-carboxamide derivatives using 2,2-dimethyl-2H,4H-1,3-dioxin-4-ones by microwave irradiation
Miriyala, Bruhaspathy,Williamson, John S.
, p. 7957 - 7959 (2007/10/03)
A general, efficient and rapid method for the synthesis of various β-carboxamide derivatives using microwave irradiation is described. Excellent isolated yields were obtained in very short reaction times when conventional heating was replaced by microwave irradiation.
A New Route to 6-Azachromones. An Improved Synthesis of 2-Azaxanthone
Cordonnier, Guy,Sliwa, Henri
, p. 111 - 115 (2007/10/02)
Condensation of the morpholine enamine of 1-benzyl-4-piperidone with β-ketoesters yielded 6-azatetrahydrochromones which were debenzylated and aromatized to 6-azachromones; 2-azaxanthone has been thus obtained with an improved yield as compared to previous syntheses.
Enamines; 44. 2-Acyl-1,1-diamino-ethenes. A New Source of Methylketones, β-Keto Amides and β-Keto Esters
Armati, Antonella,Ruggieri, Pietro De,Rossi, Elisabetta,Stradi, Riccardo
, p. 573 - 576 (2007/10/02)
A general synthesis of 2-acyl-1,1-diamino-ethenes by reaction of 1,1-dimorpholino- and 1,1-dipiperidino-ethenes with aliphatic and aromatic acyl chlorides and their utilization as a source of methylketones, β-keto amides and β-keto esters is reported.
