586418-54-4

Upstream product

• 814-49-3 diethyl chlorophosphate 
• 125617-18-7 3-(4-trifluoromethylphenyl)-2-propen-1-ol 
• 101466-85-7 ethyl (E)-4-trifluoromethylcinnamate 
• 455-19-6 4-Trifluoromethylbenzaldehyde 

Downstream Products

• 1581720-42-4 (2S,3S)-N-benzyl-2-(dimethylamino)-3-(4-(trifluoromethyl)phenyl)pent-4-enamide 
• 945684-76-4 (R)-[1-(4-trifluoromethylphenyl)allyl]dimethylphenylsilane 
• 1161928-81-9 C₁₈H₁₆F₃N 
• 1346130-59-3 (S)-N-(1-(4-(trifluoromethyl)phenyl)allyl)-2-vinylaniline 

Relevant academic research and scientific papers

Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement

A tandem relay catalytic protocol using both Pd and isothiourea catalysis has been developed for the enantioselective synthesis of α-amino acid derivatives containing two stereogenic centers from readily accessible N,N-disubstituted glycine aryl esters and allylic phosphates. The optimized process uses a bench-stable succinimide-based Pd precatalyst (FurCat) to promote Pd-catalyzed allylic ammonium salt generation from the allylic phosphate and the glycine aryl ester. Subsequent in situ enantioselective [2,3]-sigmatropic rearrangement catalyzed by the isothiourea benzotetramisole forms syn-α-amino acid derivatives with high diastereo- and enantioselectivity. This methodology is most effective using 4-nitrophenylglycine esters and tolerates a variety of substituted cinnamic and styrenyl allylic ethyl phosphates. The use of challenging unsymmetrical N-allyl-N-methylglycine esters is also tolerated under the catalytic relay conditions without compromising stereoselectivity.

Asymmetric synthesis of α-chiral allylic silanes by enantioconvergent γ-selective copper(I)-catalyzed Allylic Silylation

Gamma way: Regio- and enantioselective allylic substitution with a silicon nucleophile generated by copper(I)-catalyzed Si-B bond activation provides direct access to α-chiral allylic silanes from linear acceptors. The enantioconvergent catalysis employing McQuade's six-membered N-heterocyclic-carbene-copper(I) catalyst is applicable to aryl- and alkyl-substituted allylic phosphates (see scheme). Copyright

Synthesis of β-substituted α-amino acids with use of iridium-catalyzed asymmetric allylic substitution

The asymmetric synthesis of β-substituted α-amino acids with use of iridium-catalyzed allylic substitution was described. The Ir-catalyzed allylic substitution of diphenylimino glycinate with allylic phosphates proceeded smoothly even at 0 °C and gave branch products with high enantioselectivity (up to 97% ee), when chiral bidentate phosphite bearing the 2-ethylthioethyl group was employed. In addition, both diastereomers of the branch products were synthesized stereoselectively by simply switching the base employed. These methods were also applied to the asymmetric synthesis of quaternary α-amino acids.