190076-24-5

Upstream product

• 180684-58-6 N,N-Dibenzylphenylalanine benzyl ester 
• 1795-98-8 rac-phenylalaninol 
• 100-39-0 benzyl bromide 
• 171815-91-1 N,N-dibenzyl phenylalanin ethyl ester 
• 111138-83-1 N,N-dibenzyl-L-phenylalanine benzyl ester 
• 300-57-2 allylbenzene 
• 52742-32-2 N,N-dibenzyl-O-benzoylhydroxylamine 
• 73183-34-3 bis(pinacol)diborane 
• 150-30-1 Phenylalanine 

Downstream Products

• 1350909-98-6 tert-butyl (RS,E)-4-(N,N-dibenzylamino)-5-phenylpent-2-enoate 
• 1350910-18-7 tert-butyl (3R,4R,αS)-3-[N-3',4'-dimethoxybenzyl-N-(α-methylbenzyl)amino]-4-(N,N-dibenzylamino)-5-phenylpentanoate 
• 1010729-23-3 N,N-dibenzyl-N-(2-bromo-3-phenylpropyl)amine 
• 123808-74-2 (rac)-2-(dibenzylamino)-3-phenylpropionaldehyde 

Relevant academic research and scientific papers

A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered "soft"copper(I) hydrides to previously unreactive "hard"ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.

Copper/bisphosphine catalysts in the internally borylative aminoboration of unactivated terminal alkenes with bis(pinacolato)diboron

Cu(I)/modified dppbz catalyst systems for the regioselective aminoboration of unactivated terminal alkenes have been developed. The bisphosphine-based Cu catalysis enables the introduction of the readily transformable Bpin group at the more congested inte

A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-Γ-aminated nitroalkenes derived from L-α-amino acids

New chiral (S,E)-γ-N,N-dibenzylated nitroalkenes 2a-c were synthesized from natural L-(α)-amino acids in five steps with overall yields of 68-88%. The conjugate addition of hydride, methoxide, nitronate and azide nucleophiles to 2a-c led to the corresponding chiral 1,3-nitroamines in 74-90% yield. The conjugate addition of cyanide anion to 2a,b was followed by HNO2 elimination affording chiral aminated acrylonitriles (73-98%). On the other hand, the azide anion reacted with 2a, in acetonitrile, via a [3 + 2]-cycloaddition in which HNO2 was lost, providing the corresponding 1,2,3-triazole derivative. Direct reduction of 1,3- nitroamine derivatives 9a,b produced the corresponding 1,3-diamines in good yields.

Parallel kinetic resolution of acyclic γ-amino-α,β- unsaturated esters: Application to the asymmetric synthesis of 4-aminopyrrolidin-2-ones

Conjugate addition of a 50:50 pseudoenantiomeric mixture of lithium (R)-N-benzyl-N-(α-methylbenzyl)amide and lithium (S)-N-3,4- dimethoxybenzyl-N-(α-methylbenzyl)amide to a range of racemic acyclic γ-amino-α,β-unsaturated esters (derived from the corresponding α-amino acids) effects their efficient parallel kinetic resolution, allowing the preparation of enantiopure β,γ-diamino esters. The β,γ-diamino ester products of these reactions are readily converted into the corresponding substituted 4-aminopyrrolidin-2-ones via N-debenzylation and cyclization.

Efficient synthesis of functionalized aziridinium salts

(Chemical Equation Presented) Various aziridinium salts were efficiently prepared from bromination of a series of backbone substituted N,N-bisubstituted β-amino alcohols and isolated via flash column chromatography. The effect of C-substitution, N-substitution, solvent, leaving group, and counter-anions on formation of the isolable aziridinium salts was investigated. 2009 American Chemical Society.

Differential cleavage of arylmethyl ethers: Reactivity of 2,6-dimethoxybenzyl ethers

CrCl2/LiI selectively cleave benzyl ethers and methoxy-substituted benzyl ethers (see scheme) in the order: C6H5CH2OR 6H4CH2OR 2C6H3CH2OR 2C6H3CH2OR. In contrast, C6H5CH2OR is more readily cleaved than 2,6-(MeO)2C6H3CH2OR during catalytic hydrogenolysis while 3,4-(MeO)2C6H3CH2OR is cleaved faster than 2,6-(MeO)2C6H3CH2OR with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

Investigation of the configurational stability of lithiated phosphine oxides using the Hoffmann test: X-ray structures of (2S*,3S*,4R*)-2-(N,N-dibenzylamino)-4-diphenylphosphinoyl-1- phenylpentan-3-ol and (2S*,4S*)-2-(N,N-dibenzylamino)-4-diphenylphosphinoyl-1- phenylpentan-3-one

The Hoffmann test (reaction of a racemic organolithium with a phenylalanine-derived aldehyde) is used to show that lithiated diphenylphosphine oxides are not configurationally stable in THF at -78°C (usual reaction conditions) on the timescale of their rate of reaction with the aldehyde. The test is carried out by reacting lithiated ethyldiphenylphosphine oxide with a phenylalanine-derived aldehyde and because all four diastereoisomeric alcohols are obtained, it is necessary to determine the relative stereochemistry of the products. This is done using a combination of synthesis and X-ray crystallography of (2S*,3S*,4R*)-2-(N,N-dibenzylamino)-4-diphenylphosphinoyl-1- phenylpentan-3-ol and(2S*,4S*)-2-(N,N-dibenzylamino)-2-diphenylphosphinoyl-1- phenylpentan-3-one.