1095607-09-2

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 1428339-77-8 (2S,4R)-3-[(2R)-2-fluoro-3-phenylpropanoyl]-4-phenyl-2-trifluoromethyloxazolidine 

Downstream Products

• 1116118-88-7 (R)-1-(2-fluoro-3-phenylpropyl)-4-(pyridin-2-yl)piperazine 
• 1116118-87-6 (R)-1-(1-(2-fluoro-3-phenylpropyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one 
• 1116118-90-1 (R)-8-(2-fluoro-3-phenylpropyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one 
• 1116118-91-2 (R)-N-benzyl-2-fluoro-3-phenylpropan-1-amine 
• 1116118-89-8 (R)-5-chloro-1-(1-(2-fluoro-3-phenylpropyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one 
• 1095607-35-4 (S)-4-benzyl-3-{(2S,3S,4R)-4-fluoro-3-hydroxy-2-methyl-5-phenylpentanoyl}oxazolidin-2-one 
• 146805-76-7 (R)-2-fluoro-3-phenylpropionic acid 
• 1443226-41-2 (3R)-3-fluoro-4-phenylbutan-1-amine 
• 1443226-31-0 (2R)-2-fluoro-3-phenylbutanenitrile 
• 1335302-58-3 (1S,2R)-2-fluoro-1,3-diphenylpropan-1-amine 
• 1335302-57-2 tert-butyl 4-((2R,3R,4R)-3-((R)-1,1-dimethylethylsulfinamido)-4-fluoro-2-hydroxy-5-phenylpentyl)piperidine-1-carboxylate 
• 1335302-56-1 (R)-N-((2S,3R,4R)-1-(benzyloxy)-4-fluoro-2-hydroxy-5-phenylpentan-3-yl)-2-methylpropane-2-sulfinamide 
• 1335302-54-9 (R)-N-((1R,2R,3R)-1-cyclopropyl-3-fluoro-1-hydroxy-4-phenylbutan-2-yl)-2-methylpropane-2-sulfinamide 
• 1335302-51-6 (R)-N-((2R,3S)-2-fluoro-1-phenylhexa-4,5-dien-3-yl)-2-methylpropane-2-sulfinamide 

Relevant academic research and scientific papers

Diastereoselective Synthesis of C2′-Fluorinated Nucleoside Analogues Using an Acyclic Approach

Nucleoside analogues bearing a fluorine in the C2′-position have been synthesized by SN2-like cyclizations of acyclic thioaminal precursors. This strategy provides access to two scaffolds, d-1′,2′-cis-thiofuranosides and d-1′,2′-trans-furanosides, which are difficult to generate using the standard approach for nucleoside synthesis. The addition of silylated nucleobases onto model C2-fluorinated dithioacetal substrates resulted in 1,2-syn diastereoselectivity, which is consistent with the C2-F and S-alkyl moiety being in close proximity. A new series of analogues bearing a C3′ all-carbon quaternary center along with a C2′-F atom have also been synthesized using this approach and are being investigated as potential antimetabolites.

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

Highly diastereoselective synthesis of enantioenriched: Anti -α-allyl-β-fluoroamines

A highly diastereoselective synthesis of anti-α-allyl-β-fluoroamines has been developed involving enantioselective α-fluorination of aldehydes followed by a diastereoselective Petasis allyl borono-Mannich reaction. The products are obtained generally in g

Organomediated Enantioselective 18F Fluorination for PET Applications

The first organomediated asymmetric 18F fluorination has been accomplished using a chiral imidazolidinone and [18F]N-fluorobenzenesulfonimide. The method provides access to enantioenriched 18F-labeled α-fluoroaldehydes (>90 % ee), which are versatile chiral 18F synthons for the synthesis of radiotracers. The utility of this process is demonstrated with the synthesis of the PET (positron emission tomography) tracer (2S,4S)-4-[18F]fluoroglutamic acid.

Crystallization-induced dynamic resolution of fox chiral auxiliary and application to the diastereoselective electrophilic fluorination of amide enolates

A highly efficient crystallization-induced dynamic resolution (CIDR) of trans-Fox (fluorinated oxazolidine) chiral auxiliary is reported. This chiral auxiliary was used for highly diastereoselective (>98% de) electrophilic fluorination of amide enolates. After removal of the chiral auxiliary, highly valuable enantiopure α-fluorocarboxylic acids and β-fluoroalcohols are obtained.

A general, enantioselective synthesis of β- And γ-fluoroamines

In this Letter, we describe a short, high yielding protocol for the enantioselective (87-96% ee) and general synthesis of β-fluoroamines and previously difficult to access γ-fluoroamines from commercial aldehydes via organocatalysis.

Highly diastereoselective and general synthesis of primary β-fluoroamines

A short, high yielding protocol has been developed for the highly diastereoselective (dr >20:1) and general synthesis of primary β-fluoroamines by the enantioselective α-fluorination of aldehydes, conversion into the N-sulfinyl aldimine, nucleophilic addi

Rapid, general access to chiral β-fluoroamines and β,β-difluoroamines via organocatalysis

A rapid, general route to enantiopure β-fluoroamines and β,β-difluoroamines has been developed employing organocatalysis in both a twopot and a one-pot procedure. Both chemical yields (64-82%) and enantioselectivity (94-98% ee) were excellent and represen

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.

Direct asymmetric α-fluorination of aldehydes

(Chemical Equation Presented) Linear and branched aldehydes are asymmetrically α-fluorinated with L-proline and pyrrolidine-based organocatalysts (see scheme; NFSi: N-fluorobenzenesulfonamide). In the first case, yields and enantioselectivities were high;