326804-18-6Relevant academic research and scientific papers
Ionic-surfactant-coated subtilisin: Activity, enantioselectivity, and application to dynamic kinetic resolution of secondary alcohols
Kim, Kyungwoo,Lee, Eungyeong,Kim, Cheolwoo,Park, Jaiwook,Kim, Mahn-Joo
, p. 8836 - 8844 (2017)
In this work, we explored the utility of ionic-surfactant-coated Bacillus licheniformis subtilisin (ISCBLS) as the catalyst for the dynamic kinetic resolution of secondary alcohols. ISCBLS was prepared by freeze-drying Bacillus licheniformis subtilisin wi
Free and immobilized lecitase ultra as the biocatalyst in the kinetic resolution of (E)‐4‐arylbut‐3‐en‐2‐yl esters
Chojnacka, Anna,Drozd, Rados?aw,G?adkowski, Witold,Le?niarek, Aleksandra,Szymańska, Magdalena
, (2020/03/17)
The influence of buffer type, co‐solvent type, and acyl chain length was investigated for the enantioselective hydrolysis of racemic 4‐arylbut‐3‐en‐2‐yl esters using Lecitase Ultra (LU). Immobilized preparations of the Lecitase Ultra enzyme had
Enantioselective synthesis of α-methyl carboxylic acids from readily available starting materials via chemoenzymatic dynamic kinetic resolution
Thalen, Lisa K.,Sumic, Anna,Bogar, Krisztian,Norinder, Jakob,Persson, Andreas K. Ae.,Baeckvall, Jan-E.
scheme or table, p. 6842 - 6847 (2010/11/24)
An enantioselective method for the synthesis of α-methyl carboxylic acids starting from trans-cinnamaldehyde, a readily available and inexpensive compound, has been developed. Allylic alcohol 1 was obtained via a standard Grignard addition to trans-cinnamaldehyde. Dynamic kinetic resolution was applied to allylic alcohol 1 utilizing a ruthenium catalyst and either an (R)-selective lipase or an (S)-selective protease to provide the corresponding allylic esters in high yield and high ee. A copper-catalyzed allylic substitution was then applied to provide the corresponding alkenes with inversion of stereochemistry. Subsequent C-C double bond cleavage afforded pharmaceutically important α-methyl substituted carboxylic acids in high ee and overall yields of up to 76%.
Enzyme Reactions in Apolar Solvent. 5. The Effect of Adjacent Unsaturation on the PPL-Catalyzed Kinetic Resolution of Secondary Alcohols
Morgan, Brian,Oehlschlager, Allan C.,Stokes, Thomas M.
, p. 3231 - 3236 (2007/10/02)
The effect of adjacent unsaturation on the enzyme-catalyzed kinetic resolution of secondary alcohols is studied for a series of allylic, homoallylic, propargylic, homopropargylic, and phenyl-substituted 2-alkanols, using porcine pancreatic lipase (PPL) in anhydrous Et2O.Excellent enantioselectivity (high E value) was observed for α-phenethyl alcohol (3), propargylic alcohols (8 and 11), and (E)-allylic alcohols (9 and 12), but (Z)-allylic alcohols (10 and 13) showed poor selectivity.Enantioselectivity was also low for both (E)- and (Z)-homoallylic alcohols (15 and 16), homopropargylic alcohol (14), 1-phenyl-2-propanol (6), and 4-phenyl- 2-butanol (7).The enhanced enantioselectivity observed for (E)-allylic alcohols was exploited in the synthesis of the enantiomers of both components of the aggregation pheromone of the lesser grain borer, Rhyzopertha dominica (F.).The magnitude of the enantiomeric ratio (E value) can be dramatically affected by the accuracy of the values of ees and eep used in the calculation, especially when E is large.Variation in the value of E with the optical purity of the chiral derivatizing agent used to determine ees and eep is illustrated.
