56246-59-4

Upstream product

• 1713-33-3 1,2-epoxy-1-methylcyclohexane 
• 591-49-1 1-methylcyclohex-1-ene 
• 1713-33-3 cis-1,2-epoxy-1-methylcyclohexane 

Downstream Products

• 54826-45-8 endo-2-methylcyclohex-2-en-1-yl benzoate 
• 20461-30-7 2-methylcyclohex-2-en-1-ol 
• 4065-80-9 2-methylenecyclohexanol 

Relevant academic research and scientific papers

Stereo- and regioselectivity in the P450-catalyzed oxidative tandem difunctionalization of 1-methylcyclohexene

The selective partial oxidation of small non-functionalized molecules using biocatalysis based on P450 monooxygenases is known to be difficult due to the expected poor regio- and stereoselectivity, but in this study it was nevertheless attempted. 1-Methyl

Manipulating the Expression Rate and Enantioselectivity of an Epoxide Hydrolase by Using Directed Evolution

We describe here a strategy to improve the expression efficiency and enantioselectivity of Aspergillus niger epoxide hydrolase (ANEH) by directed evolution. Based on a blue-colony screening system using the LacZα (β-galactosidase α peptide) complementation solubility reporter, several ANEH variants out of 15000 transformants from a random-mutagenesis library were identified that show improved recombinant expression in E. coli. Among them, Pro221Ser was subsequently used as a template for iterative saturation mutagenesis (ISM) at sites around the ANEH binding pocket. Following four rounds of ISM, a highly enantioselective mutant was identified that catalyzes the hydrolytic kinetic resolution of racemic glycidyl phenyl ether with a selectivity factor of E=160 in favor of the (S)-diol compared to WT ANEH characterized by E=4.6. Expression of this mutant is 50 times higher than that of WT ANEH. It also serves as an excellent stereoselective catalyst in the hydrolytic kinetic resolution and desymmetrization of several other structurally diverse epoxides. Copyright

Epoxidation process using amine catalysts

A process for the epoxidation of an alkene, which process comprises reaction of an alkene with an oxidising agent in the presence of a catalyst, characterised in that the catalyst is an amine of formula (I), wherein T represents hydrogen or a moiety of formula (a); R1, R2, R3, R4, R5 and R6 each independently represents hydrogen, optionally substituted alkyl, an optionally substituted aryl group, heterocyclyl or an optionally substituted aralkyl group wherein substituents for the above mentioned groups are selected from up to three of alkyl, aryl, heterocycyl, hydroxy, alkoxy or a group NRsRt wherein R5 and Rt each independently represents hydrogen, alkyl or alkylcarbonyl and R7 represents hydrogen, alkyl, aryl or aralkyl; or T represents a moiety (a) wherein R1 together with R2 represents an optionally substituted alkylene chain comprising 2 to 6 carbon atoms the alkylene chain being optionally interrupted with an oxygen atom or a group NRp wherein Rp is hydrogen or alkyl, and wherein optional substituents for any carbon atom of the alkylene chain are selected from hydroxy, alkoxy, oxo or a group NRsRt wherein Rs and Rt each independently represents hydrogen, alkyl or alkylcarbonyl or substituents on any two adjacent carbon atoms of the chain together with the carbon atoms to which they are attached form an alicyclic, aryl or heterocyclic ring; and R3, R4, R5, R6 and R7 are as defined above.

Novel Catalytic Kinetic Resolution of Racemic Epoxides to Allylic Alcohols

(Matrix Presented) The kinetic resolution of racemic epoxides via catalytic enantioselective rearrangement to allylic alcohols was investigated. Using the Li-salt of (1S,3R,4R)-3-(pyrrolidinyl)methyl-2-azabicyclo [2.2.1] heptane 1 as catalyst allowed both

Allylic alcohols via catalytic asymmetric epoxide rearrangement

Epoxides using chiral lithium amides, but other than for a small subset of meso-epoxides, insufficient reactivity and enantioselectivity hamper the existing methods. Furthermore, the chiral reagents are often required in large excess. This study presents a general and highly enantioselective process that, in addition, is based on catalytic amounts (5 mol %) of enantiopure (1S,3R,4R)-3-(1-pyrrolidinyl)methyl-2-azabicyclo[2.2.1]heptane and lithium diisopropylamide as the stoichiometric base. The influence of structural modification of the catalyst is studied in terms of activity, enantioselectivity, and aggregation behavior. The utility of the process is demonstrated by its application to a variety of epoxide derivatives (≥94% ee for 11 out of 14 examples), including the formal syntheses of, e.g., a prostaglandin core unit, epibatidine, carbovir, faranal, and lasiol. The system is readily extended to the resolution of racemic epoxides, which allows access to highly enantioenriched epoxides or allylic alcohols, even at conversions near 50%.

Chemoenzymic resolution and deracemisation of (±)-1-methyl-1,2- epoxycyclohexane: The synthesis of (1-S, 2-S)-1-methylcyclohexane-1,2-diol

Corynebacterium C12 epoxide hydrolase transforms (±)-1-methyl-1,2-epoxy-cyclohexane 1 to the (1-S, 2-S)-1-methylcyclohexane-1,2-diol 2 leaving the (1-S, 2-R)-epoxide 3 unchanged. The diol 2 is converted to the (1-R, 2-S)-epoxide 4 by sulfonation-ring closure. A one pot combination of Corynebacterium C12 epoxide hydrolase and acid catalysed ring opening converts (±)-1-methyl-1,2-epoxycyclohexane 1 to (1-S, 2-S)-1-methylcyclohexane-1,2-diol 2.