67715-14-4

Upstream product

• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 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 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 98-79-3 L-Pyroglutamic acid 
• 511543-55-8 (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octane-4,8-dione 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 261951-64-8 (2S)-5-oxopyrrolidine-2-carboxylic acid (R)-1-phenylethylamide 

Downstream Products

• 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 
• 1621189-50-1 (S)-2-[(R)-1-phenylethyl]tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione 
• 1621189-32-9 (S)-2-[(R)-1-phenylethyl]-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2-ium hexafluorophosphate 

Relevant academic research and scientific papers

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.

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.

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

Synthesis and characterization of chiral 1,2-diamines from 5-oxo-pyrrolidine-(S)-2-carboxylic acid

Unsymmetrical chiral secondary vicinal diamines were synthesized by applying a modified three-step reaction. The key step in this sequence is a primary amine mediated ring opening reaction of a diastereomeric oxazolidinone derivative. A possible mechanism

Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline

Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N-methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields.