131971-63-6Relevant articles and documents
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
The role of proton shuttling mechanisms in solvent-free and catalyst-free acetalization reactions of imines
Lillo, Victor J.,Mansilla, Javier,Saá, José M.
supporting information, p. 4527 - 4536 (2018/06/29)
Proton transfer is central to the understanding of chemical processes. More so in addition reactions of the type NuH + E → Nu-EH taking place under solvent-free and catalyst-free conditions. Herein we show that the addition of alcohols or amines (the NuH component) to imine derivatives (the E component), in 1:1 ratio, under solvent-free and catalyst-free conditions, are efficient methods to access N,O and N,N-acetal derivatives. In addition, computational studies reveal that they are catalyzed reactions involving two or even three NuH molecules operating in a cooperative manner as H-bonded NuH?(NuH)n?NuH associates (many body effects) in the transition state through a concerted proton shuttling mechanism (addition of alcohols) or stepwise proton shuttling mechanism (addition of amines), thereby facilitating the key proton transfer step.
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.
A New Method for the Synthesis of N-t-Butoxycarbonyl protected α-Alkoxy Amines from Allylamines under Neutral Conditions
Nemoto, Hisao,Jimenez, Hermogenes N.,Yamamoto, Yoshinori
, p. 1304 - 1306 (2007/10/02)
Treatment of the Boc protected allylamines (4) with rhodium catalysts in the presence of alcohols produces N-Boc substituted α-alkoxy amines (5) in high yields, which can be used as a synthetic equivalents of activated imines having an easily deprotectable Boc group.
