211614-09-4

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 565-53-7 ethyl dibromofluoroacetate 
• 1479-22-7 ethyl 2-fluoro-3-oxo-3-phenylpropionate 
• 910803-66-6 ethyl α-(1,3-benzothiazol-2-ylsulfonyl)-α-fluoroacetate 
• 1160968-12-6 ethyl 2-fluoro-2-(pyrimidin-2-ylsulfonyl)acetate 
• 149-30-4 2-Mercaptobenzothiazole 
• 590365-58-5 triethyl 2-fluoro-3-oxo-5-phenyl-2-phosphonopentanoate 
• 590365-63-2 ethyl 2-diethylphosphono-2-fluoro-3-hydroxy-5-phenylpentanoate 
• 2356-16-3 ethyl(diethylphosphono)(fluoro)acetate 

Downstream Products

• 1582802-63-8 (Z)-(5-Bromo-4-fluoropent-3-enyl)benzene 
• 1333325-91-9 (Z)-2-fluoro-5-phenylpent-2-enoic acid 

Relevant academic research and scientific papers

Organocatalyzed Sulfa-Michael Addition of Thiophenols on Trisubstituted α-Fluoroacrylates, a Straightforward Access to Chiral Fluorinated Compounds

In this manuscript, a simple and efficient sulfa-Michael addition reaction of aryl thiols to trisubstituted α-fluoro-α,β-unsaturated esters both in racemic and, for the first time, in enantioselective version is reported. The commercially available dimer of cinchona derivatives (DHQ)2PYR was used as a catalyst. This strategy showed a great tolerance for various substrates and substituents, providing fair to excellent yields, moderate to excellent diastereoselectivities (2:1 to >99:1), and low to good enantioselectivities (2 to 87%). The reaction has been applied to the synthesis of fluorinated analogues of diltiazem and tiazesim, both therapeutic agents.

Stereoselective formation of (Z)-2-fluoroalkenoates via Julia-Kocienski reaction of aldehydes with pyrimidinyl-fluorosulfones

The selective synthesis of fluoroalkenoates is reported from a pyrimidinyl fluorosulfone. This sulfone allowed the preparation of Z-fluoroalkenoates with very high stereoselectivity from both aromatic and aliphatic aldehydes. The nature of the heterocycle

A facile and mild approach for stereoselective synthesis of α-fluoro-α,β-unsaturated esters from α-fluoro-β-keto esters via deacylation

The highly stereoselective olefination reaction of α-fluoro-β-keto esters for the synthesis of α-fluoro-α,β-unsaturated esters has been developed. The olefination combines nucleophilic addition, intramolecular nucleophilic addition, and elimination in one step, as well as provides a facile synthetic approach to α-fluoro-α,β-unsaturated esters which are important units in many biologically active compounds and useful precursors in a variety of functional-group transformations.

Pd-and Cu-catalyzed stereo-and regiocontrolled decarboxylative/C-H fluoroalkenylation of heteroarenes

Pd/Cu-catalyzed decarboxylative/direct C-H alkenylations of heteroarenes with α-fluoroacrylic acid is reported. This method offers step-economical and stereocontrolled access to valuable heteroarylated monofluoroalkenes as both Z and E isomers, which are known to be useful in the synthesis of fluorinated biomolecules.

Diethylzinc-mediated one-step stereoselective synthesis of α-fluoroacrylates from aldehydes and ketones. Two different pathways depending on the carbonyl partner

(Chemical Equation Presented) A efficient methodology allowing the one-pot stereoselective synthesis of R-fluoroacrylates, based on the addition of ethyl dibromofluoroacetate to a carbonyl derivative using diethylzinc as organometallic mediator, is descri

Tandem reduction-olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates and a synthetic approach to Cbz-Gly-Ψ[(Z)-CF{double bond, long}C]-Gly dipeptide isostere

(Z)-α-Fluoro-α,β-unsaturated esters (Z)-7a-f were stereoselectively prepared by a tandem reduction-olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates 6a-f with NaBH4 in EtOH. A concise synthesis of Cbz-Gly-Ψ[(Z)-CF{double bond, long}C]-Gly (26) as a dipeptide isostere was achieved via the tandem reduction-olefination of the corresponding 2-acyl-2-fluoro-2-phosphonoacetate 20.

Efficient synthesis of fluoroalkenes via diethylzinc-promoted wittig reaction

The synthesis of α-fluoroacrylates and α-bromo-α- fluoroalkenes was achieved in very good yields using aldehydes and ketones, triphenylphosphine, diethylzinc as promoter, and ethyl dibromofluoroacetate or dibromofluoromethane, respectively. A change in th

Z-selective or stereospecific alkenylation reaction: A novel synthetic method for α-fluoro-α,β-unsaturated esters

The Z-selective formation of α-fluoro-α,β-unsaturated esters was achieved using the deselenenic acid of the syn-and/or anti-3-aryl-2-fluoro-3-hydroxy-2-organoselanylacetates 3 and 4 with trifluoromethanesulfonic acid. In contrast, the 3-alkyl-substituted propanoates 3f and 4b stereospecifically underwent alkenylation to give the (E)- or (Z)-α-fluoro-α,β-unstaurated esters 5f. We were also successful in the one-pot alkenylation reactions. Copyright

Synthesis of dihalohydrins and tri- and tetra-substituted olefins

A novel synthesis reaction for highly stereospecific tri- and tetra-substituted olefins is described. A single stereoisomer of stable α-halo-α,β-ester is produced in high yield by the reaction of aldehyde or ketone with a trihalogenated compound such as t

Tandem reduction-olefination for the stereoselective synthesis of (Z)-α-fluoro-α,β-unsaturated esters

A tandem stereoselective reduction-olefination reaction of ethyl 2-acyl-2-fluoro-2-diethylphosphonoacetate employing NaBH4 in EtOH was developed. The one-pot reaction gave α-fluoro-α,β-unsaturated esters with excellent (Z)-selectivity. A plausible mechanism involving a diastereoselective reduction predicted by the Felkin-Anh model, followed by olefination similar to the Horner-Wadsworth-Emmons reaction, has been proposed.