146329-67-1Relevant articles and documents
Synthesis of chiral α-Alkoxyketones via allene oxides
Shipman, Michael,Thorpe, Heidi R.,Clemens, Ian R.
, p. 897 - 900 (1997)
Treatment of enantiemerically enriched epoxy mesylates 7-9 with potassium alkoxides under carefully controlled reaction conditions (18-crown-6, THF, -78°C) provide the coresponding α-alkoxyketones 10-13 without significant racemisation. The reactions are shown to proceed with net stereochemicaI inversion at the epoxide centre.
Chemoenzymatic synthesis of 'α-bichiral' synthons. Application to the preparation of chiral epoxides
Besse,Veschambre
, p. 1271 - 1285 (1993)
Microbiological reduction of 3-bromo-2-octanone and 3-azido-2-octanone led to all the stereoisomers of 3-bromo-2-octanol and 3-azido-2-octanol. Chiral 2,3-epoxyoctanes were prepared from the 3-bromo-2-octanols.
Generation of odorous acyloins by yeast pyruvate decarboxylases and their occurrence in sherry and soy sauce
Neuser, Frauke,Zorn, Holger,Berger, Ralf G.
, p. 6191 - 6195 (2000)
Volatile acyloins (α-hydroxy ketones) were obtained by condensing either aldehydes with pyruvate or 2-keto acids with acetaldehyde in a reaction catalyzed by yeast pyruvate decarboxylases (EC 4.1.1.1). Odor qualities and threshold values of 34 acyloins were evaluated, and 23 of them possessed distinct flavor properties. Sherry and soy sauce flavors were analyzed: 2-hydroxy-3-pentanone and 3-hydroxy-2-pentanone were identified in soy sauce for the first time; these and 2-hydroxy-5-methyl-3-hexanone and 3-hydroxy-1-phenyl-2-butanone were isolated from sherry for the first time. The biocatalytic efficiencies of crude pyruvate decarboxylase preparations from Zygosaccharomyces bisporus, Saccharomyces cerevisiae, Kluyveromyces lactis, and Kluyveromyces marxianus were compared. Product yields comparable to those of conversions with purified pyruvate decarboxylase demonstrated the suitability of crude enzyme extracts as cost-effective biocatalysts in acyloin formation. Conversion rates of >50% showed that the potential of this type of enzyme to catalyze the formation of aliphatic acyloins has been underestimated before.
Thermodynamic favorable CO2 conversion via vicinal diols and propargylic alcohols: A metal-free catalytic method
Han, Li-Hua,Li, Jing-Yuan,Song, Qing-Wen,Zhang, Kan,Zhang, Qian-Xia,Sun, Xiao-Fang,Liu, Ping
supporting information, p. 341 - 344 (2019/07/04)
Organocatalysis represents a promising field in chemical fixation of CO2. Herein, a facile metal-free strategy was reported for the one-pot preparation of cyclic carbonates and α-hydroxy ketones from vicinal diols, propargylic alcohols and CO2. Wide scope of vicinal diols and propargylic alcohols was demonstrated to be efficient under the DBU-catalyzed conditions. A plausible mechanism was proposed, which included detailed main and side reactions under the metal-free conditions.
Selective Synthesis of Unsymmetrical Aliphatic Acyloins through Oxidation of Iridium Enolates
Sanz-Marco, Amparo,Martinez-Erro, Samuel,Martín-Matute, Belén
supporting information, p. 11564 - 11567 (2018/07/31)
The first method to access unsymmetrical aliphatic acyloins is presented. The method relies on a fast 1,3-hydride shift mediated by an IrIII complex in allylic alcohols followed by oxidation with TEMPO+. The direct conversion of allylic alcohols into acyloins is achieved in a one-pot procedure. Further functionalization of the Cα′ of the α-amino-oxylated ketone products gives access to highly functionalized unsymmetrical aliphatic ketones, which further highlights the utility of this transformation.
