943784-90-5

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 3105-95-1 pipecolinic acid 
• 147-85-3 L-proline 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 84890-94-8 (S)-2-Isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 24544-04-5 2,6-diisopropylbenzenamine 

Downstream Products

• 1005495-75-9 C₃₇H₅₆N₄O₂ 
• 1253594-35-2 (S)-2,6-diisopropyl-N-(pyrrolidin-2-ylmethyl)aniline 
• 1281987-84-5 C₂₁H₃₄N₂O₂S 
• 1621189-28-3 (S)-2-(2,6-diisopropylphenyl)-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2-ium hexafluorophosphate 
• 1621189-49-8 (S)-2-(2,6-diisopropylphenyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-3(2H)-thione 
• 1621189-47-6 (7aS,7'aS,E)-2,2'-bis(2,6-diisopropylphenyl)-1,1',2,2',5,5',6,6',7,7',7a,7'a-dodecahydro-3,3'-bipyrrolo[1,2-c]imidazolylidene 
• 1313735-04-4 C₂₄H₃₂N₂O₂ 

Relevant academic research and scientific papers

Chiral bisformamides as effective organocatalysts for the asymmetric one-pot, three-component strecker reaction

(Chemical Equation Presented) C2-symmetric chiral bisformamides have been shown to catalyze the asymmetric one-pot, three-component Strecker reaction, which produced the α-amino nitriles in excellent yields (up to 99%) with good enantioselectiv

Modular synthesis of new bicyclic carbene precursors

A series of new N-heterocyclic carbene (NHC) precursors, containing bicyclic pyrrolo[1,2-c]imidazole framework, were prepared from N-(tert-butoxycarbonyl)-L-proline (1-Boc-L-proline). The sequential attachment of nitrogen nucleophiles and subsequent ring

Chiral azo-heterocyclic carbene precursor compound with bicyclic framework and preparation method thereof

The invention discloses a chiral azo-heterocyclic carbene precursor compound with a bicyclic framework and a preparation method thereof. A series of the chiral azo-heterocyclic carbene precursor compound with the bicyclic framework is obtained by taking c

Enantioselective Synthesis of 2,2,3-Trisubstituted Indolines via Bimetallic Relay Catalysis of α-Diazoketones with Enones

An efficient asymmetric intramolecular trapping of ammonium ylides of α-diazoketones with enones to synthesize indoline derivatives was realized. A Rh(II)/chiral N,N′-dioxide-Sc(III) complex bimetallic relay catalytic system was established. A series of optically active 2,2,3-trisubstituted indolines were obtained in high yields (up to 99%), good enantioselectivities (up to 99% ee), and excellent diastereoselectivities (up to >19:1 dr) under mild reaction conditions.

Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane

Catalytic asymmetric reduction of N-unsubstituted β-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted β-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of β-aryl- and β-alkyl-substituted free β-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.

Asymmetric transfer hydrogenation reaction in water: Comparison of chiral proline amide/amine ruthenium(II) complexes

Chiral proline amide/amine ligands (2, 3), synthesized by multi-step reaction starting from l-proline (1), were evaluated as catalyst generated in situ from [RuCl2(p-cymene)]2 for asymmetric transfer hydrogenation of aromatic ketones in the presence of sodium formiate and sodium dodecyl sulfate (SDS). The results revealed that efficiencies and enantioselectivities strongly depend on the N-substituents.

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.

Chiral lewis base catalyzed highly enantioselective reduction of N-alkyl β-enamino esters with trichlorosilane and water

First, test the water! In the presence of a chiral Lewis base catalyst 2, the supposedly moisture-unfriendly reduction system with trichlorosilane was found to be highly efficient and enantioselective when using water as an additive. For the first time, this method enables the reduction of a broad range of N-alkyl β-enamino esters 1 to give N-alkyl β-amino esters 3 in good to high yields and with excellent enantioselectivities (see scheme).

Cross-coupling reactions of aryl halides with amines, phenols, and thiols catalyzed by an N,N′-dioxide-copper(I) catalytic system

The coupling reactions of various N, O, and S nucleophilic reagents with aryl halides have been successfully carried out under mild conditions by using a novel chiral N,N′-dioxide-copper(I) catalytic system as the catalyst. This versatile and efficient catalyst system has been demonstrated to facilitate the cross-coupling reactions of aryl halides with amines, phenols, and thiols to afford the corresponding desired products in good to excellent yields.

A novel chiral aliphatic-aromatic diamine promoted direct, highly enantio- and diastereoselective Michael addition of cyclohexanone to nitroolefins under solvent-free conditions

A series of new highly efficient chiral aliphatic-aromatic diamine catalysts have been designed and successfully applied to the asymmetric Michael addition of cyclohexanone with nitroolefins under solvent-free conditions without any acidic additives. The desired adducts were obtained in high yields with excellent enantio- and diastereoselectivities of syn products (up to >99% ee, >99:1 dr).