514214-80-3

Upstream product

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 66866-46-4 C₁₅H₂₇NO₆ 
• 13734-41-3 t-Boc-L-valine 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 72-18-4 L-valine 

Downstream Products

• 1357570-05-8 C₂₃H₃₅N₃O₄ 
• 1357570-06-9 C₂₆H₃₆F₃N₃O₅ 
• 1357569-99-3 C₂₄H₃₂F₃N₃O₄ 
• 80650-85-7 (S)-2-amino-3-methyl-N-[(R)-1-phenylethyl]butanamide 
• 1375257-30-9 (S)-3-methyl-N₁-[(R)-1-phenylethyl]butane-1,2-diamine 
• 1375257-29-6 (S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one 
• 1375257-24-1 N-acetyl-(S)-4-isopropyl-1-[(R)-1-phenylethyl] imidazolidin-2-one 
• 1375257-32-1 (S)-3-[(S)-3-hydroxy-3-phenylpropanoyl]-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one 
• 1375257-39-8 (S)-3-[(S)-3-(4-fluorophenyl)-3-hydroxypropanoyl]-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one 
• 1375257-41-2 (S)-3-[(S)-3-(4-chlorophenyl)-3-hydroxypropanoyl]-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one 
• 1375257-43-4 (S)-3-[(S)-3-(2-chlorophenyl)-3-hydroxypropanoyl]-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one 
• 1375257-44-5 (S)-3-[(S)-3-(4-bromophenyl)-3-hydroxypropanoyl]-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one 
• 1375257-45-6 (S)-3-[(S)-3-(4-methylphenyl)-3-hydroxypropanoyl]-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one 
• 1375257-46-7 (S)-3-[(S)-3-(2-methoxyphenyl)-3-hydroxypropanoyl]-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one 

Relevant academic research and scientific papers

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.

A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation

The development of peptide-based oxidation catalysts that use a transiently generated dioxirane as the chemically active species is reported. The active catalyst is a chiral trifluoromethyl ketone (Tfk) with a pendant carboxylic acid that can be readily incorporated into a peptide. These peptides were capable of epoxidizing alkenes in high yield (up to 89%) and enantiomeric ratios (er) ranging from 69.0:31.0 to 91.0:9.0, depending on the alkene substitution pattern.

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

Employing the structural diversity of nature: Development of modular dipeptide-analogue ligands for ruthenium-catalyzed enantioselective transfer hydrogenation of ketones

A library of novel dipeptideanalogue ligands based on the combination of tert-butoxycarbonyl(N-Boc)-protected a-amino acids and chiral vicinal amino alcohols were prepared. These highly modular ligands were combined with [{RuCl2(p-cymene)}2 and the resulting metal complexes were screened as catalysts for the enantioselective reduction of acetophenone under transfer hydrogenation conditions using 2-propanol as the hydrogen donor. Excellent enantioselectivity of 1-phenylethanol (up to 98% ee) was achieved with several of the novel catalysts. Although most of the ligands contained two stereocenters, it was demonstrated that the absolute configuration of the product alcohol was determined by the configuration of the amino acid part of the ligand. Employing ligands based on L-amino acids generated S-configured products, and catalysts based on Damino acids favored the formation of the R-configured alcohol. The combination N-Boc-L-alanine and (R)-phenylglycinol (Boc-L-Ab) or its enantiomer (N-Boc-D-alanine and (S)-phenylglycinol, Boc-D-Aa) proved to be the best ligands for the reduction process. Transfer hydrogenation of a number of aryl alkyl ketones were evaluated and excellent enantioselectivity, up to 96 % ee, was obtained.