115182-22-4

Upstream product

• 108-05-4 vinyl acetate 
• 104388-31-0 (S)-1-Cyclohex-1-enyl-pyrrolidine-2-carboxylic acid diethylamide 
• 104388-30-9 ((S)-1-Cyclohex-1-enyl-pyrrolidin-2-yl)-pyrrolidin-1-yl-methanone 
• 591-87-7 Allyl acetate 
• 130203-12-2 (S)-1-Cyclohex-1-enyl-2-[(diphenylphosphanyl)-methyl]-pyrrolidine 
• 583-04-0 vinyl benzoate 
• 15727-80-7 allyl 4-nitrobenzoate 
• 4873-09-0 allyl tosylate 
• 130203-10-0 allyl o-toluenesulfonate 
• 130409-58-4 2-allylcyclohex-1-en-1-yl acetate 
• 123532-30-9 1-(propionyloxy)-2-allylcyclohexene 
• 24738-82-7 (S)-1-Cyclohex-1-enyl-pyrrolidine-2-carboxylic acid ethyl ester 
• 1746-13-0 allyl phenyl ether 
• 86448-82-0 (+)-erythro-N-cyclohexylidene-2-methoxy-1,2-diphenylethylamine 

Downstream Products

• 21895-83-0 (±)-(1S,2R)-2-allylcyclohexanol 
• 21895-83-0 (1R,2R)-2-allylcyclohexanol 
• 464919-50-4 (+)-cis-1-[2-isopropenyl-2-(triethylsiloxy)cyclohexyl]-3,4-dimethylpent-3-en-2-ol 
• 464919-79-7 (-)-(1R,2R)-[2-isopropenyl-2-(triethylsiloxy)cyclohexyl]acetaldehyde 
• 464919-91-3 (-)-(1R,2R)-(2-allyl-1-isopropenylcyclohexyloxy)triethylsilane 
• 464919-78-6 (-)-(1R,2R)-2-allyl-1-isopropenylcyclohexanol 

Relevant academic research and scientific papers

Enantiface-differentiating Enzymatic Hydrolysis of α-Substituted Cycloalkanone Enol Esters

2-Substituted 1-acyloxycycloalkenes have been hydrolysed with the aid of a micro-organism to afford optically active 2-substituted cycloalkanones.

Direct catalytic intermolecular α-allylic alkylation of aldehydes by combination of transition-metal and organocatalysis

(Chemical Equation Presented) All in the same pot together: The direct catalytic α-allylic alkylation of aldehydes and cyclic ketones is achieved by using a simple, unprecedented one-pot procedure. Transition-metal and enamine catalysis are combined so that α-allylic alkylated aldehydes and cyclic ketones are formed in high yield with a direct catalytic chemo- and regioselective method.

Palladium-catalysed Asymmetric Allylations by a Chiral Allyl Ester; the Palladium Catalysis of (S)-Proline Allyl Ester Enamines

The palladium-catalysed allylation of the chiral enamines (1a-d) followed by acidic hydrolysis, produced optically active 2-allylcyclohexanone (2); the catalysis of the chiral enamine (1a), derived from (S)-proline allyl ester, with tetrakis(triphenyl pho

Preparation of optically active ketones via enantioface-differentiating protonation of prochiral enolates

Enantioselective protonation of the prochiral lithium enolate (2) of 2-benzylcyclohexanone (3) was developed. Reaction of 2 with methyl (S)-α-hydroxyisocaproate (15) as a chiral proton source afforded (R)-3 in a high optical yield. This reaction is widely applicable to the preparation of various α-substituted optically active ketones.

Palladium-catalyzed stereoselective allylic alkylation of lithium enolates

The lithium enolates, generated from cyclohexanone, cyclopentanone, and 1-tetralone, react with allyl acetate 1b or carbonate 1c enantioselectively, when catalyzed by (R)- or (S)-BINAP-derived palladium complexes. The presence of lithium chloride is cruci

Deracemization of 2-alkylcyclohexanones utilizing host-guest molecular association with optically active host compounds in basic suspension media

Based on host-guest inclusion complexation in the solid state, α- substituted cyclohexanones 2α-c were deracemized using optically active host compounds in alkaline conditions to optically active 2 in excellent chemical yield with high enantiomeric excess.

Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones

The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.

First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer–Villiger monooxygenases

Abstract: This study investigates the substrate profile of cycloalkanone monooxygenase and 2-oxo-Δ3-4,5,5-trimethylcyclopentenylacetyl-coenzyme A monooxygenase, two recently discovered enzymes of the Baeyer–Villiger monooxygenase family, used as whole-cell biocatalysts. Biooxidations of a diverse set of ketones were performed on analytical scale: desymmetrization of substituted prochiral cyclobutanones and cyclohexanones, regiodivergent oxidation of terpenones and bicyclic ketones, as well as kinetic resolution of racemic cycloketones. We demonstrated the applicability of the title enzymes in the enantioselective synthesis of (R)-(?)-Taniguchi lactone, a building block for the preparation of various natural product analogs such as ent-quinine. Graphical abstract: [Figure not available: see fulltext.]

Enantioselective oxidation by a cyclohexanone monooxygenase from the xenobiotic-degrading Polaromonas sp. strain JS666

A cyclohexanone monooxygenase (CHMO) from the xenobiotic-degrading Polaromonas sp. strain JS666 was heterologously expressed in Escherichia coli, and its ability to catalyze enantio- and regiodivergent oxidations of prochiral and racemic ketones was investigated. The expression system was also used to evaluate this enzyme's potential role in the oxidation of cis-1,2-dichloroethene (cDCE), a groundwater pollutant for which strain JS666 is the only known assimilator. The substrate enantiopreference and -selectivity of the strain JS666 CHMO is similar to that of other CHMO-type enzymes; of note is this enzyme's excellent stereodiscrimination of 2-substituted cyclic ketones. The expression system exhibits no activity with ethene or cDCE as substrates under the tested conditions. Phylogenetic analysis shows that sequence variability among cyclohexanone monooxygenases could be a rich source of new enzyme activities and attributes.

A facile and practical method of preparing optically active α-monosubstituted cycloalkanones by thermodynamically controlled deracemization

Racemic 2-monosubstituted cycloalkanones were converted to R-isomers when TADDOLs (e.g., 1a, b) were used as host molecules in alkaline aqueous MeOH. The efficiency of this thermodynamically controlled deracemization was strongly influenced by the mixture ratio of the solvent, H2O/MeOH. Based on this finding, an improved method of preparing (R)-2-monosubstituted cycloalkanones with higher optical purity was developed. For example, (R)-2-(4-methylbenzyl)cyclohexanone (5) was obtained in 85% yield with 98% ee, when a 1:1 mixture of H2O/MeOH was used as the solvent in the presence of 1a.