33490-62-9

Upstream product

• 186581-53-3 diazomethane 
• 33490-60-7 (N-phenylbenzimidoyl) formic acid 
• 121-45-9 phosphorous acid trimethyl ester 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 62-53-3 aniline 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 4358-87-6 (RS)-methyl mandelate 
• 22979-35-7 Methyl phenyldiazoacetate 
• 622-37-7 Phenyl azide 
• 64464-76-2 methyl 2-phenyl-2-(phenylamino)acetate 
• 100-65-2 N-Phenylhydroxylamine 
• 586-96-9 Nitrosobenzene 
• 101-41-7 benzeneacetic acid methyl ester 

Downstream Products

• 64464-76-2 methyl 2-phenyl-2-(phenylamino)acetate 
• 119492-43-2 2-(phenylamino)-2-phenylethanol 
• 119566-46-0 methyl (R)-2-phenyl-2-(phenylamino)acetate 
• 1586007-58-0 (S,E)-methyl 2-(N-ethyl-N-phenylamino)-2,5-diphenylpent-4-enoate 
• 1086109-68-3 methyl 2-(N-ethyl-N-phenylamino)-3-oxo-2-phenylbutanoate 

Relevant academic research and scientific papers

A conceptually new and straightforward method for the one-pot transformation of alcohols into amines

A conceptually new amination method of alcohols has been developed using α-hydroxy esters as substrates and N-phenyl bis-trifluoromethanesulfonimide (PhNTf2) as a test reagent. Playing two roles at once, PhNTf2 activates the hydroxyl group as a highly reactive triflate intermediate and introduces the amino functionality through an in situ nucleophilic substitution by the anionic residue PhTfN-. Two complementary procedures (methods A and B herein) have been developed, the latter permitting reaction of substrates with unstable alcoxides.

Nitrone/Imine Selectivity Switch in Base-Catalysed Reaction of Aryl Acetic Acid Esters with Nitrosoarenes: Joint Experimental and Computational Study

Herein we report a mild and diastereoselective access to ketonitrones by reacting easily available aryl acetic acid esters and other active methylene compounds, with nitrosoarenes under catalytic loading of 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) at room temperature. Depending on the substitution pattern and nature of the aryl moiety, a switch toward the formation of imines can be observed. The mechanistic framework is put to scrutiny by experimental and theoretical studies, pointing to the formation of a nitroso aldol intermediate, whose fate toward one of the competing pathways, namely hydride transfer or elimination, would depend upon the NOH/CHα relative acidities. (Figure presented.).

Rhodium-Catalyzed C=N Bond Formation through a Rebound Hydrolysis Mechanism and Application in β-Lactam Synthesis

A rhodium-catalyzed reaction of N-hydroxyanilines with diazo compounds to produce α-imino esters was developed. Distinct from the commonly accepted 1,2-H transfer for normal X-H insertion reactions, density functional theory calculations indicate that this transformation proceeds via a novel rebound hydrolysis mechanism. Furthermore, a three-component reaction was explored to synthesize highly functionalized β-lactams in good yields and diastereoselectivities.

Ir-catalyzed Asymmetric Hydrogenation of α-Imino Esters with Chiral Ferrocenylphosphine-Phosphoramidite Ligands

An Ir-catalyzed asymmetric hydrogenation of α-imino esters with unsymmetrical hybrid chiral ferrocenylphosphine-phosphoramidite ligands for the synthesis of optically active α-aryl glycines has been described. The result indicated that the presence of the iodo-substitutent at the 3/3’-position of the binaphthyl unit of ligand could significantly improve the catalytic performance. This method features high asymmetric induction and reasonable functional group tolerance, thus providing a concise and efficient approach toward chiral α-aryl glycine derivatives with up to 96% ee.

Pd-Catalyzed Three-Component Domino Reaction of Vinyl Benzoxazinanones for Regioselective and Stereoselective Synthesis of Allylic Sulfone-Containing Amino Acid Derivatives

A Pd-catalyzed, highly regioselective and stereoselective three-component domino allylic substitution/N-H carbene insertion reaction under mild conditions is described. This reaction demonstrates a wide substrate scope and satisfactory functional group tolerance, providing a broad range of allylic sulfone-containing amino acid derivatives. Moreover, DBU mediates highly diastereoselective cross-dehydrogenative coupling annulation of allylic sulfones without using peroxides or any metal oxidants. This developed protocol affords 7-membered ring heterocyclic compounds incorporating both sulfone-containing amino acid esters and one quaternary carbon center. Mechanistic studies indicate that an unusual umpolung of glycine occurred in this annulation.

Catalytic conversion of diazocarbonyl compounds to imines: Applications to the synthesis of tetrahydropyrimidines and β-lactams

The synthesis of α-carbonylimines by rhodium(II)-catalyzed reactions of α-diazoesters and organic azides has been developed and applied in hetero-Diels-Alder reactions to form highly functionalized tetrahydropyrimidines and in a one-pot, multicomponent transformation between aryldiazoacetates, p-anisyl azide, and an enonediazoacetate to produce β-lactams in high yields and diastereoselectivities.

Transfer hydrogenation of imines with carboxyl-tailed benzothiazoline as readily removable hydrogen donor

A benzothiazoline bearing 4-carboxyphenyl group at 2-position was developed as an efficient hydrogen donor for the transfer hydrogenation reaction. Introduction of the carboxyl group significantly facilitated the removal of the residual benzothiazoline an

Enantioselective organocatalytic transfer hydrogenation of α-imino esters by utilization of benzothiazoline as highly efficient reducing agent

Benzothiazoline was employed as an efficient and versatile reducing agent for the chiral phosphoric acid-catalyzed transfer hydrogenation of α-imino esters. The corresponding α-amino esters were furnished with excellent enantioselectivities. Novel and rea

Catalytic reductive N-alkylation of anilines. Application to the synthesis of N-aryl aminoacid precursors

Different anilines have been monoalkylated by reductive alkylation using ketones and α-ketoesters as alkylating agents with good isolated yields. This provided access to aminoacid derivatives. Diastereoselective experiments were also performed.