1072147-15-9

Upstream product

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 51-35-4 4R-4-hydroxyproline 
• 149814-40-4 (2S,4R)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid 
• 114676-91-4 1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1374161-89-3 (2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-((R)-1-phenylethylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1063998-64-0 (2S,4R)-4-Hydroxy-pyrrolidine-2-carbonyl chloride 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 

Downstream Products

• 1206228-45-6 (2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Direct asymmetric aldol reactions catalysed by trans-4-hydroxy-(S)-prolinamide in solvent-free conditions

Direct asymmetric aldol reactions between 4-nitrobenzaldehyde and cyclohexanone were catalysed by trans-4-hydroxy-(S)-prolinamide (10 mol %) in the presence of CH3COOH (10 mol %) as the co-catalyst under solvent-free conditions at 15 °C. (2S,4R)-4-Hydroxy-N-((S)-1-phenylethyl)pyrrolidine-2-carboxamide 2 efficiently catalysed the asymmetric aldol reaction to afford the product in >99% yield and with 95% ee with an anti/syn ratio of 88:12 after 18 h. The additional trans-hydroxyl group on (S)-prolinamide and (S)-1-phenylethylamine both influenced the ee of the predominant anti aldol product. Different benzaldehyde derivatives with cyclohexanone gave the corresponding aldol products in 38-89% yields and with 56-94% ee with anti/syn (100:0-71:29). Catalyst 2 can be used up to 5 continuous cycles for asymmetric aldol reactions between 4-nitrobenzaldehyde and cyclohexanone with overall 91% yield and 86% yield of anti-product with anti/syn (98:2).

Structure-reactivity studies of simple 4-hydroxyprolinamide organocatalysts in the asymmetric Michael addition reaction of aldehydes to nitroolefins

A series of simple 4-hydroxyprolinamides was synthesised and they were found to act as organocatalysts for the asymmetric conjugate addition of aldehydes to nitroolefins in excellent yields (98%), with complete diastereoselectivity (99:1, syn:anti) and enantioselectivity (98% ee for syn). Furthermore, the use of low catalyst loadings (5mol%) and a low aldehyde molar excess (1.5equivalents) were achieved. Copyright

Chiral amino amides for the ruthenium(II)-catalyzed asymmetric transfer hydrogenation reaction of ketones in water

The chiral amino amide 3 was derived from L-proline and used for the [RuCl2(p-cymene)]2-catalyzed asymmetric transfer hydrogenation of prochiral ketones performed in water. Moderate to good chemical selectivities (up to 95% yield) and enantioselectivities (up to 90% ee) were obtained in the presence of 2 mol % of TBAB (n-Bu4NBr) as the phase transfer catalyst.

SMAC MIMETIC DIMERS AND TRIMERS USEFUL AS ANTI-CANCER AGENTS

The invention provides small molecule mimics of the SMAC peptide that are dimer-like or trimer-like compounds having two or three amide-containing domains connected by a linker. These compounds are useful to promote apoptosis. The invention includes pharmaceutical compositions comprising such compounds and methods to use them to treat conditions including cancer and autoimmune disorders.