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Usage

Uses

Used in Pharmaceutical Industry:
DL-2-(TRIFLUOROMETHYL)LEUCINE is used as a building block for the synthesis of pharmaceuticals due to its unique properties conferred by the trifluoromethyl group, which can enhance the drug's efficacy and pharmacokinetics.
Used in Peptide Synthesis:
In the field of peptide chemistry, DL-2-(TRIFLUOROMETHYL)LEUCINE is utilized as a component in the construction of peptides, where its hydrophobic and electronegative characteristics can influence the peptide's structure and function.
Used in Medicinal Chemistry Research:
DL-2-(TRIFLUOROMETHYL)LEUCINE serves as a valuable research tool in medicinal chemistry, where its distinctive properties can be explored for the development of novel therapeutic agents and the understanding of molecular interactions.
Used in Organic Chemistry:
DL-2-(TRIFLUOROMETHYL)LEUCINE is also used in organic chemistry for the synthesis of various organic compounds, taking advantage of its synthetic utility and versatility in chemical reactions.

Upstream product

• 216855-74-2 (S)-ethyl 2-amino-4-methyl-2-(trifluoromethyl)pentanoate 
• 926-62-5 isobutylmagnesium bromide 
• 216855-39-9 (S)-N-(p-tolylsulfinylimino)triphenylphosphorane 
• 914939-64-3 2-(4-methoxy-phenylamino)-4-methyl-2-trifluoromethyl-pent-4-enoic acid benzyl ester 
• 216855-54-8 ethyl N-(p-tolylsulfinyl)(α-trifluoromethyl)leucinate 
• 914939-66-5 benzyl 2-amino-4-methyl-2-(trifluoromethyl)pent-4-enoate 

Relevant academic research and scientific papers

A novel synthesis of fluorine-containing quaternary amino acid derivatives via palladium-catalyzed allylation reaction

The palladium-catalyzed allylation reaction of trifluoroalanine derivatives with various allyl carbonates was examined. When N-Cbz-protected alanine derivative was employed, the desired C-monoallylated product was obtained in good yield, together with C,N

Synthesis of nonracemic α-trifluoromethyl α-amino acids from sulfinimines of trifluoropyruvate

We describe a novel and useful method for the synthesis of nonracemic α-trifluoromethyl α-amino acids (α-Tfm-AAs). Key building blocks are the sulfinimines (S)-1a and (S)-1b, prepared by Staudinger reaction from trifluoropyruvate esters and the chiral N-sulfinyl iminophosphorane (S)-8, which were treated with benzyl, allyl, and alkylmagnesium halides. The resulting diastereomeric N-sulfinyl α-Tfm α-amino esters, 12 and 13, were produced with moderate to good stereoselectivity and yields. When alkyl Grignard reagents were used, stereocontrol became progressively higher with increasing steric bulk, while reversed, though poor, stereocontrol was achieved with benzyl/allyl Grignard reagents. An explanation for the observed stereochemical outcome is proposed, on the basis of the exclusive E geometry (N-sulfinyl and CF3 trans about the C=N bond) of the chiral sulfinimines 1. This assignment is the product of structural correlation and is supported by ab initio calculations and NOE experiments. Sulfinamides 12 and 13 were transformed into a series of nonracemic α-Tfm-AAs 16-22. The sulfinyl auxiliary can be regenerated and recycled.

First method for the preparation of strongly electrophilic chiral sulfinimines, and applications in asymmetric synthesis

A new and preparatively useful method for the synthesis of non racemic α-trifluoromethyl α-amino acids is presented, using chiral sulfinimines of trifluoropyruvate as key-building blocks.

Sulfinimines of trifluoropyruvate: Novel intermediates for chiral non racemic α-trifluoromethyl α-amino acids

A new and preparatively useful method for the synthesis of non racemic α-trifluoromethyl (Tfm)α-amino acids (AAs) is presented. Key-building blocks are the sulfinimines (S)-1a,b, prepared via Staudinger reaction from trifluoropyruvic esters and the chiral N-sulfinyl iminophosphorane (S)-5, which were reacted with benzyl and alkylmagnesium halides. The resulting N- sulfinyl α-Tfm α-amino esters 6a,b and 6c-g, respectively, were produced with opposite stereoselectivity. The stereocontrol with alkyl Grignard reagents was progressively higher with increasing steric bulk. Some of the adducts 6 were transformed into a-Tfm-phenylalanine (R)-8 (with regeneration and recycling the chiral auxiliary), αTfm-leucine (S)-11c, α-Tfm-butyrine (S)-11f and α-Tfm-alanine (8),11g in two steps in one-pot.