18838-10-3Relevant academic research and scientific papers
Oxyenamides as Versatile Building Blocks for a Highly Stereoselective One-Pot Synthesis of the 1,3-Diamino-2-ol-Scaffold Containing Three Continuous Stereocenters
Bolte, Michael,Grimmer, Jennifer,Kelm, Harald,Kramer, Philipp,Krieg, Sara-Cathrin,Manolikakes, Georg
, p. 23667 - 23671 (2021)
A highly diastereoselective one-pot synthesis of the 1,3-diamino-2-alcohol unit bearing three continuous stereocenters is described. This method utilizes 2-oxyenamides as a novel type of building block for the rapid assembly of the 1,3-diamine scaffold containing an additional stereogenic oxygen functionality at the C2 position. A stereoselective preparation of the required (Z)-oxyenamides is reported as well.
SYNTHESIS AND SOME ELECTROPHILIC SUBSTITUTION REACTIONS OF 2-PHENYLOXAZOLE
Belen'kii, L. I.,Cheskis, M. A.
, p. 713 - 716 (1984)
A new synthesis of 2-phenyloxazole that includes the preparation of 2-phenyloxazoline and aromatization of the latter by the action of nickel peroxide was developed.It was established that under conditions that exclude protonation electrophilic substituti
Mechanism of an Organoboron-Catalyzed Domino Reaction: Kinetic and Computational Studies of Borinic Acid-Catalyzed Regioselective Chloroacylation of 2,3-Epoxy Alcohols
Garrett, Graham E.,Tanveer, Kashif,Taylor, Mark S.
, p. 1085 - 1095 (2017)
A mechanistic study of the borinic acid-catalyzed chloroacylation of 2,3-epoxy alcohols is presented. In this unusual mode of catalysis, the borinic acid activates the substrate toward sequential reactions with a nucleophile (epoxide ring-opening by chloride) and an electrophile (O-acylation of the resulting alkoxide). Reaction progress kinetic analysis of data obtained through in situ FTIR spectroscopy is consistent with a mechanism involving turnover-limiting acylation of a chlorohydrin-derived borinic ester. This proposal is further supported by investigations of the effects of aroyl chloride substitution on reaction rate. The kinetics experiments also shed light on the effects of chloride concentration on reaction rate and indicate that the catalyst is subject to inhibition by the product of the chloroacylation reaction. Computational modeling is employed to gain insight into the effects of the organoboron catalyst on the regioselectivities of the epoxide ring-opening and acylation steps. The density functional theory calculations provide a plausible pathway for selective chlorinolysis at C-3 and benzoylation at O-1, as is observed experimentally.
Regiospecific ring opening of N-acylaziridines by neutral hydrolysis
Besbes, Neji
, p. 6569 - 6570 (1999)
The neutral hydrolysis of N-acyl-2,2-dimethylaziridines gave rise to the amidoalcohols in 76-91% overall yields. These products resulted from the specific cleavage of the C-2-N bond.
ELECTROCHEMICAL ACYLATION AND ALKYLAMINOCARBONYLATION OF AMINES AND ALCOHOLS
Masui, Masaichiro,Ozaki, Shigeko
, p. 2867 - 2870 (1982)
Electrochemical acylation and ethylaminocarbonylation of amines and alcohols are performed by anodic oxydation of the hydroxamic acids and N-ethyl-N'-hydroxyurea, respectively, in acetonitrile at a glassy-carbon electrode.
Chemoselective hydrosilylation of carboxylic acids using a phosphine-free ruthenium complex and phenylsilane
Abhilash, Vishwanathan,Gadakh, Amol V.,Ganesh, Sambasivam,Hegde, Shivaprasad N.,Jacob, Anand,Karthik, C. S.,Lamees, Thundianandi,Mathivanan, Namachivayam,Sathiyanarayanan, Arumugam Murugan
supporting information, (2022/03/01)
A highly chemoselective hydrosilylation of carboxylic acids was achieved using a bench-stable, phosphine-free Ru-complex tethered with hemi-labile thiophene ligands as the catalyst, employing phenylsilane as the reducing agent. The methodology was further elaborated towards the one-pot synthesis of indole and benzoxazine via tandem reduction/cyclization of acid and nitro group.
Synthesis of Nitrogen-Containing Heterocycles through Catalytic Dehydrative Cyclization Reactions
Rodriguez Del Rey, Freddy O.,Floreancig, Paul E.
supporting information, p. 150 - 154 (2021/01/09)
Re2O7 in hexafluoroisopropyl alcohol provides access to cationic intermediates from alcohols through the intermediacy of perrhenate esters. This manuscript describes the application of the system to the formation of a number of weakly basic heterocyclic systems through dehydration reactions and intramolecular nucleophilic addition. The influence of the substrate structure on the reaction rates and stereocontrol is discussed with respect to intermediate ion pairs.
Preparation method and application of tenofovir derivative
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Paragraph 0045; 0047, (2021/02/13)
The invention relates to a tenofovir derivative preparation method and application, and relates to a compound represented by a general formula (I), a pharmaceutically acceptable pharmaceutical salt ora hydrate thereof, wherein R1, R2, R3, the general form
TASTE-MODIFYING COMPOUNDS AND USES THEREOF
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Page/Page column 11, (2021/02/19)
The present disclosure generally relates to compounds useful as taste modifiers, particularly as compounds useful for enhancing umami taste, and their use in various comestible products, such as food and beverage products.
Hydrogenation of Secondary Amides using Phosphane Oxide and Frustrated Lewis Pair Catalysis
K?ring, Laura,Sitte, Nikolai A.,Bursch, Markus,Grimme, Stefan,Paradies, Jan
supporting information, p. 14179 - 14183 (2021/09/03)
The metal-free catalytic hydrogenation of secondary carboxylic acid amides is developed. The reduction is realized by two new catalytic reactions. First, the amide is converted into the imidoyl chloride by triphosgene (CO(OCCl3)2) using novel phosphorus(V) catalysts. Second, the in situ generated imidoyl chlorides are hydrogenated in high yields by an FLP-catalyst. Mechanistic and quantum mechanical calculations support an autoinduced catalytic cycle for the hydrogenation with chloride acting as unusual Lewis base for FLP-mediated H2-activation.
