137894-06-5

Upstream product

• 13734-41-3 t-Boc-L-valine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 271600-32-9 [2-methyl-1-(toluene-4-sulfonyl)-propyl]-carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 72-18-4 L-valine 

Downstream Products

• 915793-69-0 N-(tert-butoxycarbonyl)-(L)-valine (S)-1-phenylethylthioamide 
• 1375257-31-0 (S)-3-methyl-N₁-[(S)-1-phenylethyl]butane-1,2-diamine 
• 1375257-25-2 (S)-3-acetyl-4-isopropyl-1-[(S)-1-phenylethyl]imidazolidin-2-one 
• 1375257-33-2 (S)-3-[(S)-3-hydroxy-3-phenylpropanoyl]-4-isopropyl-1-[(S)-1-phenylethyl]imidazolidin-2-one 
• 72-18-4 L-valine 

Relevant academic research and scientific papers

Highly Diastereoselective Metal-Free Catalytic Synthesis of Drug-Like Spiroimidazolidinone

A four-step procedure has been developed for the synthesis of (S)-3-isopropyl-1-[(R)-1-phenylethyl)- 1,4-diazaspiro[4.5]decan-2-one with high diastereoselectivity (up to 95% de) from (S)-α-aminoisovaleric acid (L-valine). Quantum chemical computations of the synthesized compound have been performed using Gaussian 09 software package.

Enantioselective synthesis of d-α-amino amides from aliphatic aldehydes

Peptides consisting of d-amino amides are highly represented among both biologically active natural products and non-natural small molecules used in therapeutic development. Chemical synthesis of d-amino amides most often involves approaches based on enzy

Highly modular dipeptide-like organocatalysts for direct asymmetric aldol reactions in brine

A novel series of dipeptide-like organocatalysts derived from proline, amino acids and primary amines have been prepared for direct asymmetric aldol reactions between various aromatic aldehydes and acetone to afford aldol products in good yields (up to 82%) and moderate enantioselectivities (up to 67% ee) with only 1 mol% of catalyst-loading in brine. Under the same conditions, the direct asymmetric aldol reactions of aromatic aldehydes and cyclohexanone give aldol products with high yields (up to 91%) and moderate to good enantioselectivities (up to 88% ee) and excellent diastereoselectivities (up to 99% dr). These organocatalysts are easily synthesized from commercially available materials in multi-gram scale with high modularity in their structural and stereogenic properties.

Reversal of selectivity in acetate aldol reactions of N-acetyl-(S)-4- isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one

Synergistic effects of the exo- and endocyclic chiral centers of an imidazolidinone-based auxiliary were investigated in the perspective of acetate aldol reactions. The reversal in diastereoselectivity was accomplished by lithium and titanium enolate reactions, which proceed through proposed open and closed transitions states, respectively. The aldol adducts were used in the stereoselective synthesis of fluoxetine.

Enantioswitchable catalysts for the asymmetric transfer hydrogenation of aryl alkyl ketones

(Chemical Equation Presented) A subtle change in the ligand structure, replacing the carbonyl oxygen with sulfur in simple α-amino acid amides, resulted in a dramatic activity and selectivity improvement in the rhodium- or ruthenium-catalyzed reduction of ketones under hydrogen transfer conditions. In addition, in most cases, a switch of the product's absolute configuration was observed on going from amides to the corresponding thioamides. Under optimized conditions, we obtained the secondary alcohol products in high yield and enantioselectivity (up to 97% ee) using only 0.25 mol % catalyst loading.

Asymmetric transfer hydrogenation using amino acid derivatives; Further studies and a mechanistic proposal

A series of investigations into the use of amino acid derivatives for the asymmetric catalysis of the transfer hydrogenation of ketones are presented. Based on the results observed, a mechanistic suggestion for the origin of the enantioselective induction