32861-47-5

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 100-46-9 benzylamine 
• 10147-11-2 propargyl benzene 
• 60416-25-3 3-(cyclohex-1-enyl)propionaldehyde 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 104-55-2 3-phenyl-propenal 
• 104-54-1 3-Phenylpropenol 

Downstream Products

• 32861-51-1 benzyl-(3-phenyl-propyl)-amine 
• 919789-43-8 2-(benzylamino)-4-phenylbutanenitrile 
• 1144468-44-9 N-benzyl-3-cyclohex-1-enylpropan-1-amine 

Relevant academic research and scientific papers

Diastereoselective synthesis of substituted diaziridines from simple ketones and aldehydes

Diastereopure substituted diaziridines from simple ketones, aldehydes and amines are here reported. These important chemical scaffolds are obtained in the presence of a weak inorganic base and hydroxylamine O-sulfonic acid (HOSA). This method introduces three stereocenters in one step to provide a wide variety of substituted diaziridines with high yields and diastereoselectivities.

Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades

The alkylation of amines with either alcohols or carboxylic acids represents a mild and safe alternative to the use of genotoxic alkyl halides and sulfonate esters. Here we report two complementary one-pot systems in which the reductive aminase (RedAm) from Aspergillus oryzae is combined with either (i) a 1° alcohol/alcohol oxidase (AO) or (ii) carboxylic acid/carboxylic acid reductase (CAR) to affect N-alkylation reactions. The application of both approaches has been exemplified with respect to substrate scope and also preparative scale synthesis. These new biocatalytic methods address issues facing alternative traditional synthetic protocols such as harsh conditions, overalkylation and complicated workup procedures.

Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: Effective conversion of amines and anilines into amides

The rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes is reported. In situ generated [(BINAP)Rh]BF4 catalyzes the one-pot isomerization/oxidative amidation of allylic alcohols or direct amidation of aldehydes using acetone or styrene as the hydrogen acceptor. The conditions are general, affording good to excellent yields with a wide array of amine and aniline nucleophiles, and chemoselective, other alcohols do not participate in the oxidation reaction. Utilization of biphasic conditions is critical, as they promote an equilibrium between the imine/enamine byproducts and the hemiaminal, which can undergo oxidation to the amide.

Calix[4]arene-diphosphite rhodium complexes in solvent-free hydroaminovinylation of olefins

Under solvent-free conditions rhodium complexes containing hemispherical diphosphites based on a calix[4]arene skeleton catalyse efficiently the hydroaminovinylation of α-olefins, thereby leading to high proportions of linear enamines/amines (when startin

Studies concerning the electrophilic amino-alkene cyclisation for the synthesis of bicyclic amines

The bromination of a series of cyclohexenyl substituted secondary amines 1a-i has been investigated using Br2, PHT and NBS. In the case of Br2 and NBS the secondary amines preferentially undergo N-bromination. In contrast, PHT cleanly affords the products of alkene dibromination. In the case of Br2 the N-bromo species then give the products of alkene dibromination, albeit less efficiently. On subsequent treatment with K2CO3 these dibromides form the corresponding hexahydroindoles 2a-h and octahydroquinoline 2i. The presence of an N-substituent bearing a stereogenic centre (1h and 1i) was studied and the products 2h and 2i were isolated with no diastereoselectivity. When NBS was used a novel cyclisation, forming bromo-substituted octahydroindoles 9a,b and d, was observed. In relation to this sequence it was shown that these products were not intermediates in the former Br2/PHT processes and that the reaction only proceeded in the presence of the succinimide by-product of N-bromination.

Controlling selectivity: From Markovnikov to anti-Markovnikov hydroamination of alkynes

A remarkable control of regioselectivity is achieved for the titanium-catalyzed intermolecular hydroamination of various alkynes. Proper choice of the ligand enables a selectivity switch from the Markovnikov to the anti-Markovnikov products from M:anti-M = > 90:10 to >10:90. Depending on the catalyst a remarkable control of regioselectivity is achieved for the titanium-catalyzed intermolecular hydroamination of various alkynes. Proper choice of sterically hindered phenol ligands such as 1 and 4 enables a selectivity switch from the Markovnikov to the anti-Markovnikov products from M:anti-M = > 90:10 to > 10:90.

Highly enantioselective and diastereoselective synthesis of β-amino acid esters and β-lactams from achiral esters and imines

The reaction of S-tert-butyl thiopropionate with a number of N-benzyl or N-allyl aldimines (4) as promoted by the chiral diazaborolidine 1 and triethylamine afforded the β-amino acid esters 5 with high diastereoselectivity and enantioselectivity, providin