140840-55-7

Upstream product

• 15870-10-7 2-methylhept-1-ene 
• 632-21-3 1,1,3,3-tetrachloropropanone 
• 110-43-0 n-pentyl methyl ketone 
• 1774-47-6 trimethylsulfoxonium iodide 
• 2181-42-2 trimethylsulphonium iodide 

Downstream Products

• 53907-75-8 (S)-2-methyl-1,2-epoxyheptane 
• 53907-75-8 (-)-(R)-1-methyl-1-pentyloxirane 
• 140923-55-3 (S)-2-methylheptane-1,2-diol 
• 107657-54-5 (R)-2-methylheptane-1,2-diol 
• 60435-70-3 2-methyl-1-heptanol 
• 16630-91-4 2-methylheptanal 
• 625-25-2 2-Methyl-2-heptanol 

Relevant academic research and scientific papers

Kinetics of two-electron oxidations by the compound I derivative of chloroperoxidase, a model for cytochrome P450 oxidants

Rate constants for two-electron oxidation reactions of Compound I from chloroperoxidase (CPO) with a variety of substrates were measured by stopped-flow kinetic techniques. The thiolate ligand of CPO Compound I activates the iron-oxo species with the resu

Iron-Catalyzed Epoxidation of Linear α-Olefins with Hydrogen Peroxide

The combination of Fe(OTf)2 with N-methyl bis(picolylamine) (Me-bpa) L7 enables epoxidation of linear olefins including terminal, internal, and cyclic ones, using hydrogen peroxide as terminal oxidant under mild conditions. In the presence of picolinic acid as additive improved yields of epoxides up to 75 % have been achieved.

Remote Amino Acid Recognition Enables Effective Hydrogen Peroxide Activation at a Manganese Oxidation Catalyst

Precise delivery of a proton plays a key role in O2 activation at iron oxygenases, enabling the crucial O?O cleavage step that generates the oxidizing high-valent metal–oxo species. Such a proton is delivered by acidic residues that may either

SYSTEMS AND METHODS FOR REGIOSELECTIVE CARBONYLATION OF 2,2-DISUBSTITUTED EPOXIDES

Provided are methods of carbonylating cyclic substrates to produce carbonyl ated cyclic products. The cyclic substrates may be 2, 2-di substituted epoxides and the cyclic products may be β,β-di substituted lactones. The method may be carried out by forming and pressurizing a reaction mixture of the cyclic substrate, a solvent, carbon monoxide, and a [LA+][CO(CO)4-] catalyst, where [LA+] is a Lewis acid capable of coordinating to the cyclic substrate. The method may proceed with a regioselectivity of 90:10 or greater. The resulting carbonylated cyclic products may be converted to ketone aldol products that retain the stereochemistry and enantiomeric ratio of the carbonyl ated cyclic products.

Regioselective Carbonylation of 2,2-Disubstituted Epoxides: An Alternative Route to Ketone-Based Aldol Products

We report the regioselective carbonylation of 2,2-disubstituted epoxides to β,β-disubstituted β-lactones. Mechanistic studies revealed epoxide ring-opening as the turnover limiting step, an insight that facilitated the development of improved reaction conditions using weakly donating, ethereal solvents. A wide range of epoxides can be carbonylated to β-lactones, which are subsequently ring-opened to produce ketone-based aldol adducts, providing an alternative to the Mukaiyama aldol reaction. Enantiopure epoxides were demonstrated to undergo the carbonylation/ring-opening process with retention of stereochemistry to form enantiopure β-hydroxy esters.

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.

METHODS FOR OBTAINING OPTICALLY ACTIVE EPOXIDES AND VICINAL DIOLS FROM 2,2-DISUBSTITUTED EPOXIDES

The invention provides yeast strains, and polypeptides encoded by genes of such yeast strains, that have enantiospecific 2,2-disubstituted epoxide hydrolase activity. The invention also features nucleic acid molecules encoding such polypeptides, vectors c

Convenient and mild epoxidation of alkenes using heterogeneous cobalt oxide catalysts

A general epoxidation of aromatic and aliphatic olefins has been developed under mild conditions using heterogeneous CoxOy-N/C (x=1,3; y=1,4) catalysts and tert-butyl hydroperoxide as the terminal oxidant. Various stilbenes and aliph

Fe(PyTACN)-catalyzed cis-dihydroxylation of olefins with hydrogen peroxide

A family of iron complexes with general formula [Fe(II)( R,Y,XPyTACN)(CF3SO3)2], where R,Y,XPyTACN=1-[2′-(4-Y-6-X-pyridyl)methyl]-4,7-dialkyl-1,4, 7-triazacyclononane, X and Y refer to the groups at positions 4 and 6 of the pyridine, respectively, and R refers to the alkyl substitution at N-4 and N-7 of the triazacyclononane ring, are shown to be catalysts for efficient and selective alkene oxidation (epoxidation and cis-dihydroxylation) employing hydrogen peroxide as oxidant. Complex [Fe(II)(Me,Me,HPyTACN)(CF 3SO3)2] (7), was identified as the most efficient and selective cis-dihydroxylation catalyst among the family. The high activity of 7 allows the oxidation of alkenes to proceed rapidly (30 min) at room temperature and under conditions where the olefin is not used in large amounts but instead is the limiting reagent. In the presence of 3 mol% of 7, 2 equiv. of H2O2 as oxidant and 15 equiv. of water, in acetonitrile solution, alkenes are cis-dihydroxylated reaching yields that might be interesting for synthetic purposes. Competition experiments show that 7 exhibits preferential selectivity towards the oxidation of cis olefins over the trans analogues, and also affords better yields and high [syn-diol]/[epoxide] ratios when cis olefins are oxidized. For aliphatic substrates, reaction yields attained with the present system compare favourably with state of the art Fe-catalyzed cis-dihydroxylation systems, and it can be regarded as an attractive complement to the iron and manganese systems described recently and which show optimum activity against electron-deficient and aromatic olefins. Copyright

Practical corey-chaykovsky epoxidation: Scope and limitation

Corey-Chaykovsky epoxidation is one of the versatile methods for synthesis of structurally diverse oxiranes. The extension of simplified Corey-Chaykovsky epoxidation has been investigated. Ketones and aromatic aldehydes were epoxidized in satisfactory to excellent yields with trimethylsulfonium iodide as an ylide precursor and crushed potassium hydroxide as a base in tertiary butanol.The scope and limitation of the simplified procedure were examined. The results revealed that the procedure is applicable to the epoxidation of ketones and aromatic aldehydes.