5204-91-1

Upstream product

• 53662-85-4 methyl tetrahydrofuran-3-carboxylate 
• 67-56-1 methanol 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 108-88-3 toluene 
• 50-00-0 formaldehyd 
• 16502-82-2 4,4-dichloro-but-3-enoic acid 
• 7664-93-9 sulfuric acid 
• 58026-12-3 dimethyl formylsuccinate 
• 50782-89-3 dimethyl 2-hydroxymethylsuccinate 

Downstream Products

• 4694-67-1 methyl (-)-(S)-5-oxotetrahydro-3-furancarboxylate 
• 4694-66-0 (-)-(S)-5-oxotetrahydro-3-furancarboxylic acid 
• 5352-72-7 (+)-(R)-5-oxotetrahydro-3-furancarboxylic acid 
• 681179-32-8 methyl (+)-(R)-5-oxotetrahydro-3-furancarboxylate 

Relevant academic research and scientific papers

Sunlight-induced C–C bond formation reaction: Radical addition of alcohols/ethers/acetals to olefins

A sunlight-induced C–C bond formation reactions upon the addition of alcohols/ethers/acetals to olefins proceeded efficiently using di-tert-butyl peroxide (DTBP). The reactions proceeded faster than many of the previously reported sunlight and many conventional lamp photolyses, typically in 3–4 h under irradiation with sunlight, in excellent yield using olefins bearing two electron withdrawing groups (EWGs) (product yield > 95 %) and in good to fair yield with olefins bearing one EWG. The yields observed for some products were ～20 % higher than those obtained using a conventional Xe lamp as the light source, which was confirmed to be due to a light intensity effect. Gram-scale experiments showed similar yields to those observed in their corresponding small-scale experiments.

Chemoenzymatic synthesis of enantioenriched 5-oxo-tetrahydro-3- furancarboxylic acid derivatives

(R)-(+)-Paraconic acid 4, (S)-(-)-terebic acid 6 and their corresponding methyl and ethyl esters having ee's ranging from 60% to 92% were obtained by enzymatic resolution of their racemates. The enzymatic resolution of racemic ethyl γ-methylparaconates 14a and 14b allowed the isolation of the unreacted ester (2R,3R)-(+)-14a and that of the lactonic acid (2S,3R)-(-)-5b with 80% and 93% ee, respectively, the former by the use of Horse liver acetone powder (HLAP), the latter using α-chymotrypsin (α-CT). The enantiomeric ethyl (2S,3S)-(-)-14a and (2S,3R)-(-)-14b, both with >99% ee, were obtained by baker's yeast reduction of diethyl acetylsuccinate.

Benzyl radicals from toluene by photosensitization with naphthalene-1,4- dicarbonitrile - Benzylation and hydroxymethylation of unsaturated compounds

In aprotic media, photoinduced electron transfer from toluene to 1,4- naphthalenedicarbonitrile (DCN) is followed by in-cage proton transfer and radical coupling. However, in the presence of a protic co-solvent, the radical ions diffuse out of the cage and deprotonation of the toluene radical cation takes place from the free solvated species. With (BuOH, this results in reductive benzylation of DCN through coupling of benzyl radicals with DCN-·. With MeOH, secondary hydrogen abstraction by PhCH2- yields hydroxymethyl radicals, which couple with DCN-·. Both benzyl and hydroxymethyl radicals are efficiently trapped by electrophilic alkenes. Thus, in the presence of dimethyl maleate, DCN-photosensitized benzylation - or hydroxy-methylation - of the substrate occurs through direct activation of the C-H bond. The same reaction has been accomplished with acrylonitrile, albeit with a lower yield.

Hydroxyalkylation and Lactone Formation from Dialkyl Malonate by Means of a EuIII/EuII Photoredox System

A EuIII/EuII photoredox system in alcohol induced an effective hydroxyalkylation at an α-position of a dialkyl malonate.The alcohol adduct was then converted to the lactone.A step-by-step hydroxyalkylation mechanism was suggested in which the Eu ion is used as a photocatalyst and also as a condensation catalyst for the reaction of dialkyl malonates and aldehydes.