149673-13-2

Upstream product

• 854139-32-5 (R,S)-2-(1-phenylethylcarbamoyl)pyrrolidine-1-carboxylic acid benzyl ester 
• 913577-88-5 (2S)-2-[((1R)-1-phenylethyl)carbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 133010-05-6 tert-butyl 2-(fluorocarbonyl)pyrrolidine-1-carboxylate 
• 167389-05-1 (2S)-2-((1S)-1-phenylethylcarbamoyl)pyrrolidine-1-carboxylic acid benzyl ester 
• 135339-67-2 (2S)-2-[((1S)-1-phenylethyl)carbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 618-36-0 rac-methylbenzylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 147-85-3 L-proline 
• 261951-62-6 (S)-N-((S)-1-phenylethyl)-5-oxopyrrolidine-2-carboxamide 
• 141874-26-2 N-Boc-(S)-proline chloride 

Downstream Products

• 67715-15-5 (S)-1-phenylethyl((S)-pyrrolidin-2-ylmethyl)amine 
• 265992-72-1 (5S)-3-[(S)-1-phenylethyl]-2-thioxo-1,3-diazabicyclo[3.3.0]octane 
• 1621189-30-7 (S)-2-[(S)-1-phenylethyl]-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2-ium hexafluorophosphate 
• 79869-86-6 (S)-1-Methyl-pyrrolidine-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide 
• 1621189-32-9 (S)-2-[(R)-1-phenylethyl]-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2-ium hexafluorophosphate 
• 1621189-50-1 (S)-2-[(R)-1-phenylethyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione 
• 1621189-48-7 (7aS,7'aS,E)-2,2'-bis[(R)-1-phenylethyl]-1,1',2,2',5,5',6,6',7,7',7a,7'a-dodecahydro-3,3'-bipyrrolo[1,2-c]imidazolylidene 

Relevant academic research and scientific papers

Synthesis and X-ray crystal structure of dichloro[S-1-phenyl-N-(S- pyrrolidin-2-ylmethyl)ethanamine]zinc(II) and its catalytic application to rac-lactide polymerization

New dichloro zinc(II) complex ligated by the homochiral bidentate ligand S-1-phenyl-N-(S-pyrrolidin-2-ylmethyl)ethanamine (PPMA) was synthesized and characterized by X-ray crystallography. The geometry of the (PPMA)ZnCl 2 is a distorted tetrahe

Synthesis, structure, and reaction of chiral 2-azidoimidazolinium salts: (7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate

Two chiral 2-azidoimidazolinium salts [(7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate (2) and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate (3)] were synthesized, and their structures were determined by X-ray single crystal structural analysis. Migratory amidation reaction of enol silyl ether with 3 proceeded, but good diastereoselectivity was not observed in the reaction.

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).

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.

A protocol for amide bond formation with electron deficient amines and sterically hindered substrates

A protocol for amide coupling by in situ formation of acyl fluorides and reaction with amines at elevated temperature has been developed and found to be efficient for coupling of sterically hindered substrates and electron deficient amines where standard methods failed.

Synthesis and characterization of new chiral azolinium salts, precursors to N-heterocyclic carbenes, derived from l-proline

A short and flexible procedure for the preparation of seven chiral azolinium and five functionalized chiral azolinium salts, precursors to N-heterocyclic carbenes, derived from l-proline has been developed. Moderate to good overall yields were obtained. Some NHC dimers and thiones were isolated. X-ray crystal structure determinations of two [Rh-NHC] complexes were also reported.

L-Pipecolinic acid derived Lewis base organocatalyst for asymmetric reduction of N-aryl imines by trichlorosilane: Effects of the side amide group on catalytic performances

A series of N-formamides derived from pipecolinic acid have been synthesized and tested as Lewis base catalysts for the enantioselective reduction of N-aryl imines by trichlorosilane. Through the investigation of the structure-efficacy relationship between the side amide group and catalytic performance, several highly effective catalysts were discovered. In particular, arylamido-type catalyst 5i and non-arylamido-type catalyst 6c exhibited high reactivity and enantioselectivity, furnishing the reduction of a wide variety of N-aryl imines with high isolated yields (up to 98%) and ee values (up to 96%) under mild conditions. Moreover, these two catalysts complement each other in terms of their tolerances to nonaromatic ketimines and non-methyl ketimines. The Royal Society of Chemistry 2013.

Pyrrolidine based chiral organocatalyst for efficient asymmetric Michael addition of cyclic ketones to β-nitrostyrenes

An efficient asymmetric Michael addition of cyclic ketones to β-nitrostyrenes using secondary diamine as an organocatalyst derived from l-proline and (R)-α-methylbenzyl amine has been described. This pyrrolidine based catalyst 1 was found to be very effec

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.

An enantioselective Biginelli reaction catalyzed by a simple chiral secondary amine and achiral Bronsted acid by a dual-activation route

An enantioselective Biginelli reaction that proceeds by a dual-activation route has been developed by using a combined catalyst of a readily available trans-4-hydroxyproline-derived secondary amine and a Bronsted acid. Aromatic, heteroaromatic, and fusedr