112654-60-1

Upstream product

• 598-21-0 2-Bromoacetyl bromide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 79-08-3 bromoacetic acid 

Downstream Products

• 22530-98-9 4-benzyl-dihydro-furan-2-one 
• 21040-45-9 Cinnamyl acetate 
• 112654-61-2 (E)-3-phenyl-2-propenyl (nitrooxy)acetate 
• 132316-71-3 trans-cinnamyl α-diazoacetate 
• 1619239-43-8 (E)-1-(2-(cinnamyloxy)-2-oxoethyl)tetrahydro-1H-thiophen-1-ium tetraphenylborate 
• 133871-04-2 (E)-cinnamyl phenylacetate 
• 169532-08-5 (1α,5α)-6β-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 71719-52-3 1-(3-Phenyl-2-propenyl)-2,2-dimethylethylen-tricarboxylat 
• 123208-56-0 (E)-3-phenyl-2-propenyl glyoxylate oxime 
• 74959-16-3 <3α,3aα>-3-phenylfuro<3,4-c>isoxazoline 
• 112654-48-5 Acetoxy-benzoylamino-acetic acid (E)-3-phenyl-allyl ester 
• 112654-64-5 Benzoylamino-hydroxy-acetic acid (E)-3-phenyl-allyl ester 
• 112654-49-6 (4R,4aS,7aR)-2,4-Diphenyl-4a,7a-dihydro-4H,5H-furo[3,4-d][1,3]oxazin-7-one 
• 112654-47-4 Oxo-acetic acid (E)-3-phenyl-allyl ester 

Relevant academic research and scientific papers

Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions

The development of non-natural reaction mechanisms is an attractive strategy for expanding the synthetic capabilities of substrate promiscuous enzymes. Here, we report an "ene"-reductase catalyzed asymmetric hydroalkylation of olefins using α-bromoketones as radical precursors. Radical initiation occurs via ground-state electron transfer from the flavin cofactor located within the enzyme active site, an underrepresented mechanism in flavin biocatalysis. Four rounds of site saturation mutagenesis were used to access a variant of the "ene"-reductase nicotinamide-dependent cyclohexanone reductase (NCR) from Zymomonas mobiles capable of catalyzing a cyclization to furnish β-chiral cyclopentanones with high levels of enantioselectivity. Additionally, wild-type NCR can catalyze intermolecular couplings with precise stereochemical control over the radical termination step. This report highlights the utility for ground-state electron transfers to enable non-natural biocatalytic C-C bond forming reactions.

Water-soluble chiral ruthenium(II) phenyloxazoline complex: Reusable and highly enantioselective catalyst for intramolecular cyclopropanation reactions

The intramolecular cyclopropanation of various trans-allylic diazoacetates and alkenyl diazoketones has been achieved with excellent enantioselectivities of up to 98% ee and in quantitative yields by using a water-soluble ruthenium(II)/hydroxymethyl(phenyl)oxazoline catalyst in a water/ether biphasic medium. The catalyst could be reused at least five times.

N,N′-ditosylhydrazine: A convenient reagent for facile synthesis of diazoacetates

A novel entry to the synthesis of diazoacetates is disclosed. A variety of diazoacetates were synthesized from the corresponding bromoacetates by treatment with N,N′-ditosylhydrazine in moderate to high yields. Ease of operation with the stable crystalline reagent as well as a short reaction time offer a useful alternative to the conventional methods.

Conversion of Unsaturated Alcohols into Functionalized Tetrahydrofurans and Tetrahydropyrans via Nitrile Oxide Dipolar Cycloadditions

The intramolecular nitrile oxide cycloaddition (INOC) of a series of unsaturated oximino ethers has been investigated.The synthesis of the olefinic nitrile oxides involves treating an unsaturated alcohol with a α-bromoalkanal O-(trimethylsilyl)oxime in the presence of fluoride ion followed by subsequent sodium hypochlorite oxidation.The nitrile oxides were not isolated but spontaneously underwent intramolecular cycloaddition to give fused five- and six-membered ring ethers.The preferred stereoisomer in the formation of the five-membered ring ethers is trans, whereasin the six-membered ring ethers the cis isomer predominates.MM2 calculations help rationalize the observed stereoselectivity.The ratio of diastereomeric products from the INOC reaction appears to correlate with product stabilities.Simple heating of some of the oximino ethers led to intramolecular cycloaddition.The ring closure apparently proceeds subsequent to a tautomeric equilibration of the oxime with a transient nitrone which is trapped by the neighboring ?-bond.

INTRAMOLECULAR CYCLOADDITION OF ALLENECARBOXYLATE. AN EFFECT OF ORBITAL OVERLAP REQUIREMENT OF THE ESTER LINKAGE

The intramolecular cyclizations of the allenecarboxylates have been examined and two types of the cycloadditions are observed.The periselectivity in these reactions was discussed on the basis of the effect of orbital overlap requirements of the ester linkage in the transition state.