131065-64-0

Upstream product

• 462-06-6 fluorobenzene 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 131101-27-4 cis-1,2-dihydroxy-3-fluorocyclohexa-3,5-diene 

Downstream Products

• 131101-31-0 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S,8S,9S)-7-fluoro-3,5-dioxo-4-phenyl-9-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl ester 
• 131043-58-8 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S,8S,9S)-7-fluoro-3,5-dioxo-4-phenyl-9-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl ester 

Relevant academic research and scientific papers

Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes

Toluene dioxygenase-catalysed oxidation of mono-substituted benzene substrates (R = F, Cl, Br, I, Me, Et, CH2OAc, CH=CH2, C=CH, CF3, CN, OMe, OEt, SMe) in growing cultures of Pseudomonas putida UV4 yielded the corresponding cis-dihydrodiol metabolites. Palladium-catalysed cross-coupling of cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene with a range of tributyltin compounds provided a chemoenzymatic route to a further series of cis-dihydrodiol derivatives of monosubstituted benzenes (R = D, CH2CH=CH2, Bun, SEt, SPr1, SBu1, SPh, SC6H4Me-4). The enantiopurities and absolute configurations of the cis-dihydrodiols, obtained by both enzymatic and chemoenzymatic routes, were determined by several new methods including 1H NMR spectroscopic analysis of the bis-MTPA esters of the 4-phenyl-1,2,4-triazoline-3,5-dione cycloadducts, X-ray crystallography, circular dichroism spectroscopy and stereochemical correlation.