136353-98-5Relevant academic research and scientific papers
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)
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
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 Mannich-type reaction of 1-(N-acylamino)alkyltriphenylphosphonium salts with silyl enolates
Pa?dzierniok-Holewa, Agnieszka,Wal?cka-Kurczyk, Alicja,Musio?, Szymon,Stecko, Sebastian
, p. 732 - 742 (2019/01/10)
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
1-(N -acylamino)alkyl sulfones from N -acyl-α-amino acids or N -alkylamides
Adamek, Jakub,Mazurkiewicz, Roman,Pazdzierniok-Holewa, Agnieszka,Grymel, Miroslawa,Kuznik, Anna,Zielinska, Katarzyna
, p. 2765 - 2770 (2014/04/17)
A variety of N-(1-methoxyalkyl)amides or carbamates react readily with sodium aryl sulfinates in the presence of triphenylphosphonium tetrafluoroborate or bromide in CHCl3 under mild conditions to give 1-(N-acylamino)alkyl sulfones in good yiel
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.
Preparation of acyclic N-acyl-N,O-acetals by decarboxylation of N-protected α-amino acids and studies of asymmetric amidoalkylation with trimethylsilyl cyanide
Harding,Liu,Farrar,Coleman,Tansey
, p. 1409 - 1417 (2007/10/02)
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.
