141022-95-9

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 826-08-4 2-fluoro 3-phenyl prop-2-ene 1-ol (Z) 
• 147410-59-1 (E)-2-fluoro-3-phenylprop-2-en-1-ol 
• 1013088-37-3 (2'S,4S)-3-(2-fluoro-3-phenyl-1-oxopropyl)-4-phenylmethyl-2-oxazolidinone 
• 458-69-5 3-phenylpropanoic acid fluoride 
• 20397-59-5 ethyl (Z)-2-fluoro-3-phenylacrylate 

Downstream Products

• 862668-88-0 (S)-(-)-2-fluoro-3-phenylpropionaldehyde 
• 297183-00-7 (S)-2-fluoro-3-phenylpropionic acid 

Relevant academic research and scientific papers

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

Highly enantioselective bioreduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae

Biocatalytic reduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae was investigated in phosphate buffer solutions. Product analysis clearly showed that (S)-2-fluoro-3-arylpropanols were afforded in high yields with up to 92% ee value.

Aldol reactions between L-erythrulose derivatives and chiral α-amino and α-fluoro aldehydes: Competition between felkin-anh and cornforth transition states

Both matched and mismatched diastereoselection have been observed in aldol reactions of a boron enolate of a protected L-erythrulose derivative with several chiral α-fluoro and α-amino aldehydes. Strict adherence to the Felkin-Anh model for the respective transition structures does not account satisfactorily for all the observed results, as previously observed in the case of α-oxygenated aldehydes. In some cases, only the Cornforth model provides a good explanation. The factors that influence this dichotomy are discussed and a general mechanistic model is proposed for aldol reactions with α-heteroatom-substituted aldehydes. Additional support for the model was obtained from density functional calculations.

Iridium catalysts with chiral imidazole-phosphine ligands for asymmetric hydrogenation of vinyl fluorides and other olefins

New chiral bidentate imidazole-phosphine ligands have been prepared and evaluated for the iridium-catalysed asymmetric hydrogenation of olefins. The imidazole-phosphine-ligated iridium catalysts hydrogenated trisubstituted olefins with the same sense of enantiodiscrimination as known iridium catalysts possessing oxazole and thiazole as N-donors. The imidazole-based catalysts were shown to hydrogenate vinyl fluorides, in some cases with the highest ee values published to date.

Iridium-catalyzed asymmetric hydrogenation of fluorinated olefins using N,P-ligands: A struggle with hydrogenolysis and selectivity

To broaden the substrate scope of asymmetric iridium-catalyzed hydrogenation, fluorine-functionalized olefins were synthesized and hydrogenated with iridium complexes. Preliminary results showed high levels of fluorine elimination together with low selectivity. The loss of vinylic fluorine at first seemed difficult to handle, but further studies revealed that a catalyst with an azanorbornyl scaffold in the ligand gave more promising results. With this in mind, a new ligand was developed. This gave among the best results published to date for fluorine asymmetric hydrogenation, yielding high conversion and very high ee's with very little fluorine elimination. Further increasing the selectivity, the trials also revealed that tetrasubstituted fluorine-containing olefins can be hydrogenated with high ee's, despite that this class of compounds has usually shown low reactivity in this reaction type. Copyright

Enantioselective formation of stereogenic carbon - Fluorine centers by a simple catalytic method

(Chemical Equation Presented) An easy protocol has been developed for the formation of stereogenic carbon-fluorine centers by the organocatalytic asymmetric α-fluorination of aldehydes 1. The 2-fluoroaldehydes 4 are formed with 2 as the fluorinating agent

A general organocatalyst for direct α-functionalization of aldehydes: Stereoselective C-C, C-N, C-F, C-Br, and C-S bond-forming reactions. Scope and mechanistic insights

The development of a general organocatalyst for the α- functionalization of aldehydes, via an enamine intermediate, is presented. Based on optically active α,α-diarylprolinol silyl ethers, the scope and applications of this catalyst for the stereogenic fo