21286-54-4Relevant articles and documents
Cremlyn,R.J.,Hornby,R.
, p. 120 - 121 (1969)
Synthesis and characterization of camphorsulfonyl acetate of cellulose
Xiao, Dingshu,Hu, Jiwen,Zhang, Mingqiu,Li, Mingwei,Wang, Guozhi,Yao, Haisong
, p. 1925 - 1931 (2004)
Novel cellulose derivatives were prepared from reacting (1R)-(+)-camphor-10-sulfonic chloride (CSC) with cellulose acetate (CA) in acetone and triethylamine. The reaction conditions, including reaction time and reactant molar ratios, were optimized. The structure of the products was confirmed by means of 1H NMR, 13C NMR, FT-IR and elementary analysis. The techniques were also used to determine the degree of the substitution of camphorsulfonyl groups (DSCS). The data calculated from 1H NMR, 13C NMR, percent grafting (G%) and elementary analysis coincided with those from chemical analysis. Compared to cellulose acetate, the cellulose derivatives exhibited decreased thermal stability, improved solubility in organic solvents and enhanced enantioselectivity towards tyrosine isomers. The solubility and enantioselectivity increased with increasing degrees of camphorsulfonyl substitution.
Modeling of the Diels-Alder reaction enantioselectivity by quantum mechanics and molecular mechanics
Zeifman, Alexey A.,Stroylov, Viktor S.,Titov, Ilya Yu.,Novikov, Fedor N.,Stroganov, Oleg V.,Svitanko, Igor V.,Chilov, Ghermes G.
, p. 269 - 270 (2015)
The enantioselectivity of the Diels-Alder reaction between (E)-3-(4-nitrophenyl)-1-(pyridin-3-yl)prop-2-en-1-one and cyclopenta-1,3-diene in the chiral ionic liquids 3-butyl-1-methylimidazolium (S)-camphorsulfonate and (S)-1-methyl-3-(pyrrolidin-2-ylmethyl)- imidazolium tosylate or upon chiral promotion with chiral oxazaborolidine was modeled by molecular and quantum mechanics and then experimentally studied; computations were in good agreement with the experimental data, resulting in no stereoselectivity with a chiral ionic liquid used as a co-solvent and prominent stereoselectivity upon chiral promotion.
Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides
Miklá?,Miklá?ová,Bukovsky,Horváth,Kubincová,Devínsky
, p. 29 - 37 (2014)
A group of homochiral quaternary ammonium sulfonamides bearing hydrophobic camphor derived moieties were synthesized and characterized. The described synthetic procedure is quick and efficient. The novel quaternary ammonium bromides were tested as antimicrobial and antifungal agents. They exhibited strong antimicrobial and also antifungal activity, especially N-{2-[((1S, 4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methylsulfonamido] ethyl}-N,N-dimethyltetradecan-1-aminium bromide 1c. The surface properties of prepared compounds were evaluated by surface tension measurements and critical micelle concentration (CMC) with surface tension at CMC (γCMC) was calculated.
First study of rhodium(I) complexes with chiral sulfur-containing terpenoids as catalytic systems for ketone hydrosilylation
Uvarov, Vladimir M.,de Vekki, Dimitry A.
, p. 376 - 387 (2019/12/24)
Using a “chiral pool” approach, a number of chiral thiolate and sulfide ligands based on natural terpenes and terpenoids have been synthesized in a few simple steps. Two new Rh-thiolate complexes with the formula [Rh(CO)2(μ-SR)]2 were obtained. The influence of these complexes and catalytic systems formed by combining the synthesized ligands with [Rh(CO)2(μ-Cl)]2 and [Rh(cod)(μ-Cl)]2, on the reaction rate, chemoselectivity, stereoselectivity and formation of tetraphenyldisiloxane in Rh-catalyzed asymmetric hydrosilylation of acetophenone as a model reaction have been studied. Mechanistic aspects of formation of silyl enol ether as a side product in the presence of S-containing ligands are presented.
Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones
Huynh, Uyen,McDonald, Stacey L.,Lim, Daniel,Uddin, Md. Nasir,Wengryniuk, Sarah E.,Dey, Sumit,Coltart, Don M.
, p. 12951 - 12964 (2018/11/30)
The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.