122313-52-4

Upstream product

• 67-56-1 methanol 
• 4132-86-9 N-benzyloxycarbonylalanine 
• 84713-20-2 benzyl N-vinylcarbamate 
• 69261-50-3 N-(benzyloxycarbonyl)acetamide 
• 1142-20-7 N-Cbz-Ala 

Downstream Products

• 136401-25-7 [(S)-1-((S)-5-Oxo-2,5-dihydro-furan-2-yl)-ethyl]-carbamic acid benzyl ester 
• 136401-25-7 [(S)-1-((R)-5-Oxo-2,5-dihydro-furan-2-yl)-ethyl]-carbamic acid benzyl ester 
• 82629-22-9 1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester 

Relevant academic research and scientific papers

Non-Kolbe electrolysis of

Here, we report a standardized method for the synthesis of N-protected (1-methoxyalkyl)amines by the electrochemical decarboxylative α-methoxylation of α-amino acid derivatives using the commercially available, easy-to-use, compact ElectraSyn 2.0 setup. T

Br?nsted acid catalyzed proto-functionalization of enecarbamates and enamides: A convenient route to N,O-acetals

N,O-acetals are important structures found in many bioactive natural products, and this unique organic functional group can serve as a useful synthetic precursor to the unstable N-acylimines. In this paper, a convenient route to synthesize N-carbamoyl-N,O

Catalyst-free Mannich-type reaction of 1-(N-acylamino)alkyltriphenylphosphonium salts with silyl enolates

A catalyst-free reaction of 1-(N-acylamino)alkyltriphenylphosphonium tetrafluoroborates with silyl enolates was developed to prepare β-amino carbonyl compounds. The reported method is a useful approach for the preparation of N-protected β-amino esters as

Photoredox-induced three-component Oxy-, Amino-, and Carbotrifluoromethylation of enecarbamates

A photoredox-catalzyed trifluoromethylation of enecarbamates process is reported. This pathway uses Togni's reagent as the CF3 source and follows a radical/cationic pathway. Under the optimized conditions using [Ru(bpy)3(PF6)2] as the photocatalyst, a wide range of substituted enecarbamates can readily be difunctionalized by means of various O, N, and C nucleophiles.

α-amidoalkylating agents from N-acyl-α-amino acids: 1-(N-acylamino)alkyltriphenylphosphonium salts

N-Acyl-α-amino acids were efficiently transformed in a two-step procedure into 1-N-(acylamino)alkyltriphenylphosphonium salts, new powerful α-amidoalkylating agents. The effect of the α-amino acid structure, the base used [MeONa or a silica gel-supported piperidine (SiO 2-Pip)], and the main electrolysis parameters (current density, charge consumption) on the yield and selectivity of the electrochemical decarboxylative α-methoxylation of N-acyl-α-amino acids (Hofer-Moest reaction) was investigated. For most proteinogenic and all studied unproteinogenic α-amino acids, very good results were obtained using a substoichiometric amount of SiO2-Pip as the base. Only in the cases of N-acylated cysteine, methionine, and tryptophan, attempts to carry out the Hofer-Moest reaction in the applied conditions failed, probably because of the susceptibility of these α-amino acids to an electrochemical oxidation on the side chain. The methoxy group of N-(1-methoxyalkyl)amides was effectively displaced with the triphenylphosphonium group by dissolving an equimolar amount of N-(1-methoxyalkyl)amide and triphenylphosphonium tetrafluoroborate in CH 2Cl2 at room temperature for 30 min, followed by the precipitation of 1-N-(acylamino)alkyltriphenylphosphonium salt with Et 2O.

Preparation of acyclic N-acyl-N,O-acetals by decarboxylation of N-protected α-amino acids and studies of asymmetric amidoalkylation with trimethylsilyl cyanide

Oxidative decarboxylation of N-acyl-α-amino acids with lead tetraacetate followed by treatment with methanol provides a facile method for preparation of acyclic N-acyl-N,O-acetals, which can be used in asymmetric α-amidoalkylation reactions using trimethylsilyl cyanide as nucleophile.

Palladium(II)-Assisted Carboacylation of Enamides To Produce Functionalized β-Amino Acids. Synthesis of Relays to (+/-)-Thienamycin

Alkylation of benzyl vinylcarbamate with sodium benzyl acetoacetate in the presence of palladium(II) chloride, followed by carbonylation (CO/MeOH), produced a highly functionalized β-amido ester that was converted, using conventional organic synthetic methodology, into a relay to (+/-)-thienamycin.