297183-00-7

Upstream product

• 63-91-2 L-phenylalanine 
• 457-45-4 (±)-2-fluoro-3-phenylpropanoic acid 
• 458-69-5 3-phenylpropanoic acid fluoride 
• 104-53-0 3-phenyl-propionaldehyde 
• 350-90-3 (Z/E)-2-fluoro-3-phenylprop-2-enoic acid 
• 147410-59-1 (E)-2-fluoro-3-phenylprop-2-en-1-ol 
• 826-08-4 2-fluoro 3-phenyl prop-2-ene 1-ol (Z) 
• 141022-95-9 (2S)-2-fluoro-3-phenylpropan-1-ol 

Downstream Products

• 1190832-66-6 C₁₅H₁₅FN₂O 

Relevant academic research and scientific papers

Synthetic Methods and Reactions. Part 106. Suppression of Anchimerically Assisted Rearrangement Products in the Synthesis of α-Fluorocarboxylic Acids from α-Amino Acids with 48:52 (w/w) Hydrogen Fluoride/Pyridine

Anchimerically assisted rearrangement, observed in the fluorination of some α-amino acids with 70:30 (w/w) hydrogen fluoride/pyridine (by weight) in the presence of NaNO2, is substantially or fully suppressed by using the less acidic reagent 48:52 (w/w) hydrogen fluoride/pyridine.

Cobalt-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Carboxylic Acids by Homolytic H2 Cleavage

The asymmetric hydrogenation of α,β-unsaturated carboxylic acids using readily prepared bis(phosphine) cobalt(0) 1,5-cyclooctadiene precatalysts is described. Di-, tri-, and tetra-substituted acrylic acid derivatives with various substitution patterns as well as dehydro-α-amino acid derivatives were hydrogenated with high yields and enantioselectivities, affording chiral carboxylic acids including Naproxen, (S)-Flurbiprofen, and a d-DOPA precursor. Turnover numbers of up to 200 were routinely obtained. Compatibility with common organic functional groups was observed with the reduced cobalt(0) precatalysts, and protic solvents such as methanol and isopropanol were identified as optimal. A series of bis(phosphine) cobalt(II) bis(pivalate) complexes, which bear structural similarity to state-of-the-art ruthenium(II) catalysts, were synthesized, characterized, and proved catalytically competent. X-band EPR experiments revealed bis(phosphine)cobalt(II) bis(carboxylate)s were generated in catalytic reactions and were identified as catalyst resting states. Isolation and characterization of a cobalt(II)-substrate complex from a stoichiometric reaction suggests that alkene insertion into the cobalt hydride occurred in the presence of free carboxylic acid, producing the same alkane enantiomer as that from the catalytic reaction. Deuterium labeling studies established homolytic H2 (or D2) activation by Co(0) and cis addition of H2 (or D2) across alkene double bonds, reminiscent of rhodium(I) catalysts but distinct from ruthenium(II) and nickel(II) carboxylates that operate by heterolytic H2 cleavage pathways.

Asymmetric synthesis of 1,2-fluorohydrin: Iridium catalyzed hydrogenation of fluorinated allylic alcohol

We have developed a simple protocol for the preparation of 1,2-fluorohydrin by asymmetric hydrogenation of fluorinated allylic alcohols using an efficient azabicyclo thiazole-phosphine iridium complex. The iridium-catalyzed asymmetric synthesis of chiral 1,2-fluorohydrin molecules was carried out at ambient temperature with operational simplicity, and scalability. This method was compatible with various aromatic, aliphatic, and heterocyclic fluorinated compounds as well as a variety of polyfluorinated compounds, providing the corresponding products in excellent yields and enantioselectivities. This journal is

Oxidative enantioselective α-fluorination of aliphatic aldehydes enabled by N-heterocyclic carbene catalysis

Described is the first study on oxidative enantioselective α-fluorination of simple aliphatic aldehydes enabled by N-heterocyclic carbene catalysis. N-fluorobis(phenyl)-sulfonimide serves as a an oxidant and as an "F" source. The C-F bond formation occurs

Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Bronsted acid catalysis

Highly enantioselective protonation of α-halo and alkoxy carboxylic acid-derived ketene disilyl acetals is achieved by using P-spiro chiral diaminodioxaphosphonium barfate as a Bronsted acid catalyst, where the enantiofacial discrimination by the catalyst mainly stems from the recognition of the electronic difference between two substituents on the ketene disilyl acetal.

Conformational preference in bis(porphyrin) tweezer complexes: A versatile chirality sensor for α-chiral carboxylic acids

Metallated porphyrin tweezers have demonstrated a remarkable ability to function as reporters of absolute stereochemistry for a number of different classes of organic molecules. Flexibility in binding, however, can result in an ensemble of different Exciton Coupled Circular Dichroism (ECCD) active conformations that could lead to variable results. Linker flexibility was found to be a key determinant of binding conformation. Experimental results indicate that a balance between linker flexibility and rigidity could yield an optimum porphyrin tweezer that stabilizes a common conformation for all bound chiral guests. This leads to a more simplified approach to absolute stereochemical determination of asymmetry for small organic molecules. This was demonstrated by the use of a C3-linked zincated porphyrin tweezer that yields a common conformational preference for a variety of α-chiral carboxylic acids derivatized with a diamine carrier. Copyright

THE TRANSFORMATION OF α-AMINOACIDS INTO FLUOROACIDS

The reactions of some α-aminoacids with excess sodium nitrite in polyhydrogen fluoride-pyridine are described.