54712-18-4

Upstream product

• 26735-84-2 oct-1-en-2-yl acetate 
• 108-22-5 Isopropenyl acetate 
• 4128-31-8 rac-octan-2-ol 
• 108-05-4 vinyl acetate 
• 85-44-9 phthalic anhydride 
• 629-05-0 n-octyne 
• 64-19-7 acetic acid 
• 32786-26-8 1-phenylethyl 2-methoxyacetate 

Downstream Products

• 5978-70-1 (R)-Octan-2-ol 
• 106760-31-0 (R)(-)-N,N'-dicyclohexyl-O-(1-methylheptyl)-isourea 
• 135628-86-3 (S)-(+)-2-(1-Methylheptyl)phenol 
• 103481-63-6 (S)-(+)-4-(1-Methylheptyl)phenol 
• 54739-11-6 (S)-(+)-(1-Methylheptyl) phenyl ether 

Relevant academic research and scientific papers

CO2-expanded bio-based liquids as novel solvents for enantioselective biocatalysis

For the first time, CO2-expanded bio-based liquids were reported as novel and sustainable solvents for biocatalysis. Herein, it was found that by expansion with CO2, 2-methyltetrahydrofuran (MeTHF), and other bio-based liquids, which were not favorable solvents for immobilized Candida antarctica lipase B (Novozym 435) catalyzed transesterification, were tuned into excellent reaction media. Especially, for the kinetic resolution of challenging bulky secondary substrates such as rac-1-adamantylethanol, the lipase displayed very high activity with excellent enantioselectivity (E value > 200) in CO2-expanded MeTHF (MeTHF concentration 10% v/v, 6 MPa), whereas there was almost no activity observed in conventional organic solvents.

Enzymatic kinetic resolution of aliphatic sec-alcohols by LipG9, a metagenomic lipase

Bioprospection for new enantioselective enzymes for application in organic synthesis is a prominent area of investigation in biocatalysis. In this context, here we present the evaluation of an immobilized lipase isolated from a metagenomic library (LipG9) for the enzymatic kinetic resolution (EKR) of aliphatic sec-alcohols, which are still challenging substrates, since low enantioselectivity values are usually observed for these resolutions. LipG9 was successfully employed in EKR of aliphatic alcohols, which were resolved with satisfactory conversions (19-59%) and enantiomeric excesses for alcohols (26-88%) and esters (30-96%) by transesterification reactions, demonstrating that its performance is equal to or better than commercially available enzymes for the same reaction.

Dynamic double kinetic resolution of amines and alcohols under the cocatalysis of Raney nickel/Candida antarctica lipase B: From concept to application

Herein, we have established a dynamic double kinetic resolution (DDKR) strategy under the co-catalysis of Raney nickel and Candida antarctica lipase B (CAL-B) for the one-pot simultaneous resolution of primary amines and secondary alcohols (or esters). The DDKR strategy was successfully applied to the resolution of a series of racemic amines and secondary alcohols (or esters) as well as mexiletine, an important antiarrhythmic agent. The catalysts could be recycled and reused several times with the same high activity. Scale-up experiments were also successful. As a more atom-economical and efficient process than traditional simple kinetic resolutions, the DDKR strategy can be widely used to prepare optically pure amines and alcohols.

Development of a mixed solvent system for the efficient resolution of (R, S)-2-octanol catalyzed by magnetite-immobilized lipase

In order to find a suitable reaction system for the enzymatic resolution of (R, S)-2-octanol, the effects of the molecular structure of the solvent on the enantioselectivity (E) and enzymatic activity of Yarrowia lipolytica lipase (YLL) immobilized onto magnetic nanoparticles were systematically analyzed. Both the E and enzymatic activity of the reaction in an acyclic, structurally linear solvent were higher than those in the corresponding branched chain solvent or cyclic solvent. In a mixed solvent system with acetone and carbon tetrachloride (v/v = 3:7), the immobilized YLL exhibited high enantioselectivity, activity, and reusability. The thermodynamic analysis showed that the enantiomer discrimination was enthalpy-driven at all temperatures tested. These results present new opportunities and challenges for understanding and intensifying the enzymatic resolution process of (R, S)-2-octanol by designing suitable solvent system.

Highly enantioselective Rh-catalysed hydrogenation of 1-alkyl vinyl esters using phosphine-phosphoramidite ligands

MatPhos, a good mate for hard tasks: The asymmetric hydrogenation of 1-alkyl vinyl esters, thwarted so far by mediocre ee values and low activities, can now be achieved with MatPhos/Rh catalysts with ee values of 96-99 % for a variety of substrates at low catalyst loadings (0.1-1 mol %) and under mild conditions (5-20 bar H2, room temperature). After hydrolysis, the corresponding chiral secondary alkyl alcohols can be obtained in high enantiopurities providing a general and practical route to this important product class. Copyright

Syntheses of enantiopure aliphatic secondary alcohols and acetates by bioresolution with lipase B from candida antarctica

The lipase B from Candida antarctica (Novozym 435, CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan- 2-ol (1), (±)-5-methylhexan-2-ol (3), (±)-octan-2-ol (4), (±)-heptan-3-ol (5) and (±)-oct-1- en-3-ol (6). The lipase showed excellent enantioselectivities in the transesterifications of racemic aliphatic secondary alcohols producing the enantiopure alcohols (>99% ee) and acetates (>99% ee) with good yields. Kinetic resolution of rac-alcohols was successfully achieved with CALB lipase using simple conditions, vinyl acetate as acylating agent, and hexane as non-polar solvent.

Resolution of 2-octanol via immobilized Pseudomonas sp. lipase in organic medium

Pseudomonas sp. lipase (PSL) immobilization was performed using three different protocols. Lipase immobilized on Diaion HP20 (HP20-PSL) exhibited the highest catalytic activity and stability in the kinetic resolution of racemic 2-octanol. The reaction rate of HP20-PSL was approximately 20 times higher than that of free PSL and the residual activities of HP20-PSL and free PSL were respectively 84% and 19% after incubation in the reaction medium for 72 h. A study of the effect of different reaction parameters on HP20-PSL-catalyzed resolution of (R,S)-2octanol showed that the optimal water content of the immobilized matrix and the optimal molar ratio of vinyl acetate to 2-octanol were 60 ± 5% and 2.5:1, respectively. Under the optimized reaction conditions, (S)-2-octanol of high optically purity (enantiomeric excess > 99%) could be recovered at 53% conversion rate, and HP20-PSL could be reused for ten cycles without significant decrease in its activity and enantioselectivity.

Chromatography-free enzymatic kinetic resolution of secondary alcohols

Racemic secondary alcohols were resolved by enzymatic esterification using Candida antarctica lipase B (CAL B). After derivatization of the unreacted enantiomer with phthalic anhydride, the resulting phthalic acid monoesters could be easily separated from the corresponding acetates by precipitation and filtration or distillation, thus avoiding laborious column chromatography, which is a major obstacle for large-scale reactions. This method has been successfully applied to the multigram synthesis of enantiopure pyridyl alcohols.

Asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens

A new asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens has been found. Although alcohols are not the natural substrates for this enzyme, a high R enantioselectivity was observed. Stereochemical studies showed that variations in substrate structure lead to strong variations in enantioselectivity. The highest enantioselectivities are obtained when the β-carbon of the secondary alcohol is tertiary or quaternary.

Air-stable racemization catalyst for dynamic kinetic resolution of secondary alcohols at room temperature

(Chemical Equation Presented) A novel racemization catalyst was synthesized for the dynamic kinetic resolution (DKR) of alcohols with a lipase at room temperature in the air. Furthermore, a polymer-supported derivative was also synthesized and tested as a recyclable catalyst for the aerobic DKR of alcohols.