136401-24-6Relevant articles and documents
Non-Kolbe electrolysis of
Adamek, J.,Michalak, M.,Pa?dzierniok-Holewa, A.,Wal?cka-Kurczyk, A.,Walczak, K.
, p. 2107 - 2114 (2022/02/07)
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
Catalyst-free Friedel-Crafts reaction of 1-(N-acylamino)alkyltriarylphosphonium salts with electron-rich arenes
Adamek, Jakub,W?grzyk, Anna,Krawczyk, Monika,Erfurt, Karol
, p. 2575 - 2583 (2018/04/20)
Friedel-Crafts reaction of 1-(N-acylamino)alkyltriarylphosphonium salts with arenes or heteroarenes without the need for any catalyst provided access to a wide range of biologically interesting N-(1-arylalkyl)amides or 1-arylalkylphosphonium salts which c
α-amidoalkylating agents from N-acyl-α-amino acids: 1-(N-acylamino)alkyltriphenylphosphonium salts
Mazurkiewicz, Roman,Adamek, Jakub,Pazdzierniok-Holewa, Agnieszka,Zielinska, Katarzyna,Simka, Wojciech,Gajos, Anna,Szymura, Karol
experimental part, p. 1952 - 1960 (2012/04/17)
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.