369386-17-4

Upstream product

• 478156-98-8 methyl 2-(2-(benzyloxy)phenyl)-2-diazoacetate 
• 487-26-3 (2S)-flavanone 
• 149-73-5 trimethyl orthoformate 
• 22979-35-7 Methyl phenyldiazoacetate 
• 53172-91-1 (benzyloxy)(tert-butyl)dimethylsilane 
• 58769-52-1 erythro-2.3-Diphenyl-3-hydroxypropionsaeure-methylester 
• 1431563-88-0 (2S,3S)-methyl 3-((tert-butyldimethylsilyl)oxy)-2,3-diphenylpropanoate 
• 40525-65-3 2-benzyloxyphenylacetic acid methyl ester 
• 737766-28-8 (2S,3R)-2-phenyl-3-methoxycarbonyl-2,3-dihydrobenzofuran 

Downstream Products

• 369386-24-3 (2S,3R)-3-hydroxymethyl-2-phenyl-2,3-dihydrobenzo[b]furan 

Relevant academic research and scientific papers

Enantio- and Diastereoselective Synthesis of cis-2-Aryl-3-methoxycarbonyl-2,3-dihydrobenzofurans via the Rh(II)-Catalyzed C-H Insertion Process

(Matrix Presented) The enantioselective intramolecular C-H insertion reaction of aryldiazoacetates has been explored with use of dirhodium(II) carboxylate catalysts, which incorporate N-phthaloyl- or N-benzene-fused-phthaloyl-(S)-amino acids as chiral bri

An artificial metalloenzyme with the kinetics of native enzymes

Natural enzymes contain highly evolved active sites that lead to fast rates and high selectivities. Although artificial metalloenzymes have been developed that catalyze abiological transformations with high stereoselectivity, the activities of these artificial enzymes are much lower than those of natural enzymes. Here, we report a reconstituted artificial metalloenzyme containing an iridium porphyrin that exhibits kinetic parameters similar to those of natural enzymes. In particular, variants of the P450 enzyme CYP119 containing iridium in place of iron catalyze insertions of carbenes into C-H bonds with up to 98% enantiomeric excess, 35,000 turnovers, and 2550 hours-1 turnover frequency. This activity leads to intramolecular carbene insertions into unactivated C-H bonds and intermolecular carbene insertions into C-H bonds. These results lift the restrictions on merging chemical catalysis and biocatalysis to create highly active, productive, and selective metalloenzymes for abiological reactions.

Sequential C-H functionalization reactions for the enantioselective synthesis of highly functionalized 2,3-dihydrobenzofurans

The enantioselective synthesis of 2,3-dihydrobenzofurans was achieved by using two sequential C-H functionalization reactions, a rhodium-catalyzed enantioselective intermolecular C-H insertion followed by a palladium-catalyzed C-H activation/C-O cyclization. Further diversification of the 2,3-dihydrobenzofuran structures was possible by a subsequent palladium-catalyzed intermolecular Heck-type sp2 C-H functionalization.

New insight into the mechanism of hypervalent iodine oxidation of flavanones

Flavanone (1) on oxidation with iodobenzene diacetate (PIDA) in the presence of sulfuric acid in trimethyl orthoformate (TMOF) undergoes a stereospecific ring contraction by an aryl shift to result in trans methyl 2-aryl-2,3-dihydrobenzo[b]furan-3-carboxy