5267-71-0

Upstream product

• 492-41-1 (1R,2S)-norephedrine 
• 98-88-4 benzoyl chloride 
• 38222-78-5 benzoic acid-((1RS,2RS)-2-amino-1-phenyl-propyl ester); hydrochloride 
• 38222-78-5 benzoic acid-((1RS,2SR)-2-amino-1-phenyl-propyl ester); hydrochloride 
• 93-97-0 benzoic acid anhydride 
• 614-17-5 N-ethylbenzamide 
• 65-85-0 benzoic acid 
• 5267-68-5 N-(1-oxo-1-phenylpropan-2-yl)benzamide 
• 154-41-6 erythro-1-phenyl-1-hydroxy-2-propylammonium chloride 
• 16735-19-6 2-amino-1-phenylpropan-1-one hydrochloride 
• 100-52-7 benzaldehyde 
• 26251-08-1 2-nitro-1-phenylpropan-1-ol 
• 119-51-7 1-phenyl-1,2-propanedione 2-oxime 
• 532-28-5 (RS)-mandelonitrile 

Downstream Products

• 1616-50-8 3-methyl-1-phenyl-isoquinoline 
• 46989-57-5 benzoic acid-((1RS,2RS)-2-amino-1-phenyl-propyl ester) 
• 2549-31-7 4-methyl-2,5-diphenyloxazole 
• 257952-52-6 (4S,5S)-4-methyl-2,5-diphenyl-4,5-dihydro-1,3-oxazole 
• 5267-68-5 N-(1-oxo-1-phenylpropan-2-yl)benzamide 
• 1630-31-5 cis-5-phenyl-4-methyl-1,3-thiazolidine-2-thione 
• 1592-59-2 threo-1-chloro-1-phenyl-2-propylammonium chloride 
• 1592-59-2 erythro-1-chloro-1-phenyl-2-propylammonium chloride 
• 154-41-6 threo-1-phenyl-1-hydroxy-2-propylammonium chloride 
• 78374-00-2 cis-5-phenyl-2-phenylamino-4-methyl-1,3-thiazoline 
• 78374-00-2 trans-5-phenyl-2-phenylamino-4-methyl-1,3-thiazoline 
• 78374-02-4 cis-2-diethylamino-5-phenyl-4-methyl-1,3-thiazoline 
• 78374-02-4 trans-2-diethylamino-5-phenyl-4-methyl-1,3-thiazoline 
• 78373-96-3 cis-5-phenyl-2-methoxy-4-methyl-1,3-thiazoline 

Relevant academic research and scientific papers

Direct enantioselective C(sp3)-H acylation for the synthesis of α-amino ketones

A direct enantioselective acylation of α-amino C(sp3)-H bonds with carboxylic acids has been achieved via the merger of transition metal and photoredox catalysis. This straightforward protocol enables cross-coupling of a wide range of carboxylic acids, one class of feedstock chemicals, with readily available N-alkyl benzamides to produce highly valuable α-amino ketones in high enantioselectivities under mild conditions. The synthetic utility of this method is further demonstrated by gram scale synthesis and application to late-stage functionalization. This method provides an unprecedented solution to address the challenging stereocontrol in metallaphotoredox catalysis and C(sp3)-H functionalization. Mechanistic studies suggest the α-C(sp3)-H bond of the benzamide coupling partner is cleavage by photocatalytically generated bromine radicals to form α-amino alkyl radicals, which subsequently engages in nickel-catalyzed asymmetric acylation.

Enantiomerically divergent pathways in Tsuji-Trost reactions: exploiting the structural differences between β-acyloxy-o-(diphenylphosphino)benzamides and β-amido-o-(diphenylphosphino)benzoates

Using a single chiral scaffold, (1R,2S)-norephedrine, a series of monophosphine ligands have been prepared. The ligands prepared, β-acyloxy-(o-diphenylphosphino)amides and β-amido-(o-diphenylphosphino)esters, give rise to enantiomerically divergent produc

A biocatalytic Henry reaction - The hydroxynitrile lyase from Hevea brasiliensis also catalyzes nitroaldol reactions

(Figure Presented) Novel enzyme activity: Biocatalytic Henry reactions with nitromethane and nitroethane yielded the corresponding nitroalcohols with good enantio- and diastereo-control in the presence of the hydroxynitrile lyase from the tropical rubber tree Hevea brasiliensis. Molecular modeling and deuterated starting materials were used in mechanistic investigations.

Rapid synthesis of oxazoles under microwave conditions

A new and efficient variation of the Robinson-Gabriel oxazole synthesis is described. Oxazoles were prepared by cyclodehydration of 2-acylamino carbonyl compounds with Burgess reagent under monomode microwave irradiation.

Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases

Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a meso-cyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudoephedrine was developed.

Stereoselective synthesis of 1,2-amino alcohols by asymmetric borane reduction of α-oxoketoxime ethers

Asymmetric reduction of α-oxoketoxime ethers with the reagents prepared in situ from trimethyl borate and chiral amino alcohols derived from either L-proline or α-pinene was investigated. Both cyclic and acyclic α- oxoketoxime ethers were reduced to afford the corresponding chiral 1,2amino alcohols with high enantioselectivities.

Ruthenium-catalyzed oxidations for selective syntheses of ketones and acyl cyanides. Selective acylation of amino compounds with acyl cyanides

Oxidation of alcohols to the corresponding carbonyl compounds with tert-butyl hydroperoxide in the presence of dichlorotris(triphenylphosphine)ruthenium catalyst gives the corresponding carbonyl compounds with high efficiency. This method can be applied to the oxidation of cyanohydrins to give acyl cyanides which are versatile synthetic intermediates. Acylation of amino compounds with acyl cyanides thus obtained proceeds chemoselectively. Thus, the reaction of amino alcohols with acyl cynides gives N-acylated products exclusively. In the similar N-acylation of polyamines primary amines are selectively acylated in the presence of secondary amines. These reactions are highly useful for the synthesis of spermidine and spermine alkaloids such as spermidine alkaloids such as spermidine siderophores. Dimeric cyclocoupling reaction of diacyl cyanides such as iso- and terephthaloyl cyanides with polyamines can be performed under the similar reaction conditions to give the corresponding polyazamacrocycles with high efficiency.

N-ALKYLOXAZABOROLIDINES DERIVED FROM EPHEDRINES

The synthesis of oxazaborolidines from amides derived from ephedrine and pseudoephedrine by treatment with BH3-THF is reported.The reaction affords chiral oxazaborolidines with nitrogen atom substituents of different steric requirements enlarging the pote

NON-CATALYTIC REDUCTION OF Α-OXIMINOKETONES AND Α-OXIMINOALCOHOLS TO ERYTHRO-2-AMINO-1-ARYLALKAN-1-OLS

A non-catalytic reduction of α-oximinoketones 1 and α-oximinoalcohols 2 to erythro-2-amino-1-arylalkan-1-ols 3 with lithium aluminium hydride is reported.The erythro-2-amino-1-arylalkan-1-ols are isolated as their hydrochlorides 5 and characterised as the erythro isomers by benzoylation.

STEREOCHEMICAL COURSE OF THE REACTION OF 2-HALOETHYL ISOTHIOCYANATES WITH NUCLEOPHILES. sTEREOSPECIFIC ROUTE TO 4,5-DISUBSTITUTED Δ2-THIAZOLINES AND THIAZOLIDINE-2-THIONES

Diastereoisomeric 1-chloro-1-phenyl-2-isothiocyanatopropanes have been prepared.They reacted stereospecifically with CH3ONa, diethylamine, aniline and NaSH to give pure cis or trans-4,5-disubstituted Δ2-thiazolines and thiazolidine-2-thiones whose configuration was determined using the nuclear Overhauser effect.The preponderant conformation of diastereoisomeric 1-chloro-1-phenyl-2-isothiocyanatopropanes was estimated on the basis of coupling constants of vicinal protons.