106565-48-4Relevant articles and documents
Lipase-catalysed kinetic resolutions of secondary alcohols in pressurised liquid hydrofluorocarbons
Ball, Anthony J.,Corr, Stuart,Micklefield, Jason
, p. 3543 - 3546 (2009)
Three model secondary alcohols have been subjected to enzymatic kinetic resolution using three common lipases and a typical acyl donor. The resolutions were performed in two pressurised low-boiling hydrofluorocarbons, which are novel media for enzymatic reactions, and five conventional organic solvents. In general, higher yields, ee's and rates of reaction were observed in the hydrofluorocarbons.
Highly enantioselective hydrogenation of simple ketones catalyzed by a Rh-PennPhos complex
Jiang, Qiongzhong,Jiang, Yutong,Xiao, Dengming,Cao, Ping,Zhang, Xumu
, p. 1100 - 1103 (1998)
Even alkyl methyl ketones undergo asymmetric hydrogenation with high enantioselectivity when a rhodium complex of the conformationally rigid chiral ligand 1 (Me-PennPhos; R = CH3) is used as the catalyst. Basic additives such as 2,6-lutidine contribute to the achievement of high enantiomeric excesses.
Enhancement of enantioselectivity in the optical resolution of primary alcohols with modified cyclodextrin colyophilized lipase
Shioji, Kosei,Kurauchi, Yoshimitsu,Terada, Keiko,Kodera, Yasushi,Okuma, Kentaro
, p. 2163 - 2170 (2007)
Colyophilization of lipase was carried out with immobilized β-cyclodextrins (β-CyD) bearing methyl, acetyl, benzoyl, and nicotinoyl substituents. The colyophilizates enhanced stereoselectivity in the acylation of several alcohols. The enantioselectivity in the acylation of ethyl-1-hydroxymethyl-phenylphosphine oxide using colyophilized lipase with nicotinoyl-β-CyD increased approximately threefold (from E=34 to E=113). The amphiphilic character of modified CyDs has been found to influence the enhancement of enantioselectivity. Copyright Taylor & Francis Group, LLC.
Lipase-catalyzed kinetic resolution of (±)-1-(2-furyl) ethanol in nonaqueous media
Devendran, Saravanan,Yadav, Ganapati D.
, p. 286 - 292 (2014)
S-1-(2-Furyl) ethanol serves as an important chiral building block for the preparation of various natural products, fine chemicals, and is widely used in the chemical and pharmaceutical industries. In this work, lipase-catalyzed kinetic resolution of (R/S)-1-(2-furyl) ethanol using different acyl donors was investigated. Vinyl esters are good acyl donors vis-a-vis alkyl esters for kinetic resolution. Among them, vinyl acetate was found to be the best acyl donor. Different immobilized lipases such as Rhizomucor miehei lipase, Thermomyces lanuginosus lipase, and Candida antarctica lipase B were evaluated for this reaction, among which C. antarctica lipase B, immobilized on acrylic resin (Novozym 435), was found to be the best catalyst in n-heptane as solvent. The effect of various parameters was studied in a systematic manner. Maximum conversion of 47% and enantiomeric excess of the substrate (ees) of 89% were obtained in 2 h using 5 mg of enzyme loading with an equimolar ratio of alcohol to vinyl acetate at 60C at a speed of 300 rpm in a batch reactor. From the analysis of progress curve and initial rate data, it was concluded that the reaction followed the ordered bi-bi mechanism with dead-end ester inhibition. Kinetic parameters were obtained by using nonlinear regression. This process is more economical, green, and easily scalable than the chemical processes. Chirality 26:286-292, 2014. 2014 Wiley Periodicals, Inc.
Preparation of homochiral (S)- and (R)-1-(2-furyl)ethanols by lipase-catalyzed transesterification
Kaminska, Janina,Gornicka, Iwona,Sikora, Magdalena,Gera, Jozef
, p. 907 - 910 (1996)
1-(2-Furyl)ethanol 1 was resolved by irreversible transesterification with vinyl acetate using Lipozyme IM or Porcine Pancreas Lipase (PPL) in an organic solvent. (S)-alcohol (99% e.e.) was obtained in 80-85% yield using Lipozyme IM in carbon tetrachloride while (R)-1-(2-furyl)ethyl acetate (96% e.e.) in 75-80% yield resulted from transesterification using Lipozyme IM in hexane or PPL in tetrahydrofuran.
Peracetylated β-cyclodextrin as additive in enzymatic reactions: Enhanced reaction rate and enantiomeric ratio in lipase-catalyzed transesterifications in organic solvents
Ghanem, Ashraf,Schurig, Volker
, p. 2761 - 2766 (2001)
Peracetylated β-cyclodextrin has been employed as a macrocyclic additive to enhance the enantiomeric ratio E and reaction rate in Pseudomonas cepacia lipase (PSL)-catalyzed enantioselective transesterification of 1-(2-furyl)ethanol in organic solvents. The beneficial action of the cyclodextrin used as a regulator of lipase was tentatively interpreted as increasing the conformational flexibility of the enzyme and undergoing host-guest complexation with the product, thereby preventing product inhibition and leading to an enhancement of the enantiomeric ratio E and the reaction rate. The effect of the organic solvent on the present cyclodextrin-mediated enzymatic transesterification has been studied.
Unsymmetrical Iron P-NH-P′ Catalysts for the Asymmetric Pressure Hydrogenation of Aryl Ketones
Smith, Samantha A. M.,Lagaditis, Paraskevi O.,Lüpke, Anne,Lough, Alan J.,Morris, Robert H.
, p. 7212 - 7216 (2017)
The reductive amination of α-dialkylphosphine acetaldehydes with enantiopure β-aminophosphines is a new, versatile route to unsymmetrical tridentate (pincer) ligands P-NH-P′. Four new ligands PR2CH2CH2NHCHR′CHR′′PPh2 (R=iPr, Cy, R′=Ph, CH(CH3)2, R′′=Ph, H) prepared in this way are used to make the iron(II) complexes mer-FeCl2(CO)(P-NH-P′) and mer-FeCl(H)(CO)(P-NH-P′). The hydride complex with the rigid ligand with R′=R′′=Ph is an efficient and highly enantioselective homogeneous asymmetric pressure hydrogenation (APH) catalyst. Prochiral aryl ketones are reduced under mild conditions (THF, 0.1 mol % catalyst, 1 mol % KOtBu, 5–10 bar, 50 °C) to the (S)-alcohols, usually in enantiomeric excess (ee) greater than 90 %. DFT calculations provided transition-state structures for the enantiodetermining hydride-transfer step.
Lipase-Induced Oxidative Furan Rearrangements
Blume, Fabian,Sprengart, Petra,Deska, Jan
, p. 1293 - 1296 (2018)
Lipase B from Candida antarctica catalyzes the oxidative ring expansion of furfuryl alcohols using aqueous hydrogen peroxide to yield functionalized pyranones under mild conditions. The method further allows for the preparation of corresponding piperidinone derivatives by enzymatic rearrangement of N-protected furfurylamines.
Gold- and Silver-Catalyzed Glycosylation with Pyranone Glycosyl Donors: An Efficient and Diastereoselective Synthesis of α-Anomers
Liu, Wenfeng,Chen, Qian,Liang, Jiashen,Du, Zhiyun,Zhang, Kun,Zheng, Xi,O'Doherty, George A.
, p. 1683 - 1686 (2015)
A mild, efficient and diastereoselective gold- and silver-catalyzed O-glycosylation with pyranone glycosyl donors is described. The reactions led to the formation of α-anomers in up to 91% yield with good diastereoselectivities.
A de novo approach to the synthesis of glycosylated methymycin analogues with structural and stereochemical diversity
Borisova, Svetlana A.,Guppi, Sanjeeva R.,Kim, Hak Joong,Wu, Bulan,Penn, John H.,Liu, Hung-Wen,O'Doherty, George A.
, p. 5150 - 5153 (2010)
A divergent and highly stereoselective route to 11 glycosylated methymycin analogues has been developed. The key to the success of this method was the iterative use of the Pd-catalyzed glycosylation reaction and postglycosylation transformation. This uniq
