59694-07-4Relevant academic research and scientific papers
Fast Addition of s-Block Organometallic Reagents to CO2-Derived Cyclic Carbonates at Room Temperature, Under Air, and in 2-Methyltetrahydrofuran
Elorriaga, David,de la Cruz-Martínez, Felipe,Rodríguez-álvarez, María Jesús,Lara-Sánchez, Agustín,Castro-Osma, José Antonio,García-álvarez, Joaquín
, p. 2084 - 2092 (2021/04/02)
Fast addition of highly polar organometallic reagents (RMgX/RLi) to cyclic carbonates (derived from CO2 as a sustainable C1 synthon) has been studied in 2-methyltetrahydrofuran as a green reaction medium or in the absence of external volatile organic solvents, at room temperature, and in the presence of air/moisture. These reaction conditions are generally forbidden with these highly reactive main-group organometallic compounds. The correct stoichiometry and nature of the polar organometallic alkylating or arylating reagent allows straightforward synthesis of: highly substituted tertiary alcohols, β-hydroxy esters, or symmetric ketones, working always under air and at room temperature. Finally, an unprecedented one-pot/two-step hybrid protocol is developed through combination of an Al-catalyzed cycloaddition of CO2 and propylene oxide with the concomitant fast addition of RLi reagents to the in situ and transiently formed cyclic carbonate, thus allowing indirect conversion of CO2 into the desired highly substituted tertiary alcohols without need for isolation or purification of any reaction intermediates.
Chitosan-Silica Sulfate Nano Hybrid as a Novel and Highly Proficient Heterogeneous Nano Catalyst for Regioselective Ring Opening of Epoxides via Carboxylic Acids
Behrouz, Somayeh,Soltani Rad, Mohammad Navid,Piltan, Mohammad Amin,Doroodmand, Mohammad Mahdi
, (2017/09/19)
The synthesis and characterization of chitosan-silica sulfate nano hybrid (CSSNH) as a novel and efficient heterogeneous nano catalyst involving acid-base bifunctional activity is described. The catalytic potency and activity of this eco-friendly catalyst was investigated in regioselective ring opening of epoxides with carboxylic acids to access structurally diverse 1,2-diol mono-esters in good to excellent yields. CSSNH catalyst was characterized using different microscopic and spectroscopic techniques encompassing scanning electron microscopy, transmission electron microscopy, X-ray diffraction, N2 adsorption isotherm, and Fourier transform infrared spectroscopy. The green nature, cheapness, efficiency, ease of preparation, handling and reusability of this new catalyst makes this catalyst to be useful for green industrial processes.
Stereoinversion of Stereocongested Carbocyclic Alcohols via Triflylation and Subsequent Treatment with Aqueous N,N-Dimethylformamide
Ochiai, Hidenori,Niwa, Takashi,Hosoya, Takamitsu
supporting information, p. 5982 - 5985 (2016/12/09)
A convenient method for the stereoinversion of secondary alcohols, applicable to stereocongested carbocyclic substrates, is reported. A simple three-step procedure, including triflylation of the hydroxy group, nucleophilic oxygenative displacement by the treatment with aqueous N,N-dimethylformamide (DMF), and methanolysis, allowed for efficient stereoinversion of various substrates, including sugar derivatives, in one pot.
Radical Cyclization Followed by the Fragmentation of Carbonyl Compounds: Effect of an α-Benzoyl Group
Chien, Li-An,Chang, Che-Chien
, p. 11294 - 11301 (2015/12/01)
To study a recently developed radical cyclization reaction followed by a fragmentation process in more detail, a series of α-benzoyl carbonyl compounds were prepared, including precursors with aldehyde and ketone moieties. Initiated by tributyltin hydride
I2-catalyzed regioselective oxo- and hydroxy-acyloxylation of alkenes and enol ethers: A facile access to α-acyloxyketones, esters, and diol derivatives
Reddi, Rambabu N.,Prasad, Pragati K.,Sudalai, Arumugam
supporting information, p. 5674 - 5677 (2015/02/19)
I2-catalyzed oxo-acyloxylation of alkenes and enol ethers with carboxylic acids providing for the high yield synthesis of α-acyloxyketones and esters is described. This unprecedented regioselective oxidative process employs TBHP and Et3/s
En route to multicatalysis: Kinetic resolution of trans-cycloalkane-1,2- diols via oxidative esterification
Hofmann, Christine,Schuler, Soeren M. M.,Wende, Raffael C.,Schreiner, Peter R.
supporting information, p. 1221 - 1223 (2014/01/17)
We demonstrate the application of a multicatalyst to the oxidation of a broad variety of aldehydes and subsequent enantioselective esterification of the incipient acids with (±)-trans-cycloalkane-1,2-diols. This reaction operates well with a multicatalyst bearing two independent catalytic moieties that provide monoprotected 1,2-diols in one pot.
Borinic acid-catalyzed regioselective acylation of carbohydrate derivatives
Lee, Doris,Taylor, Mark S.
supporting information; experimental part, p. 3724 - 3727 (2011/05/14)
Reversible covalent interactions of organoboron compounds are exploited as the basis for regioselective borinic acid-catalyzed acylations of polyols. This catalytic protocol enables differentiation of the secondary OH groups of a wide range of carbohydrat
An Efficient Method for the Chemoselective Preparation of Benzoylated 1,2-Diols from Epoxides
Khalafi-Nezhad,Soltani Rad,Khoshnood
, p. 2552 - 2558 (2007/10/03)
A very efficient and highly regioselective ring-opening reaction of epoxides with benzoic acid and its derivatives in the presence of cat. amount of tetrabutylammonium bromide (TBAB) in anhydrous acetonitrile has been developed. This effective method is useful for the preparation of selectively protected diols as precursor for many organic syntheses such as those of acyclic nucleosides and other synthetic purposes. The advantages of this method are efficiency, selectivity, low cost, and the applicability in large-scale synthesis of β-benzoyloxyalkanols.
Regioselective benzoylation of 6-O-protected and 4,6-O-diprotected hexopyranosides as promoted by chiral and achiral ditertiary 1,2-diamines
Hu, Guixian,Vasella, Andrea
, p. 4369 - 4391 (2007/10/03)
Monobenzoylation of triols (6-O-silylated glycopyranosides) or diols (4,6-O-benzylidenated glycopyranosides) with benzoyl chloride and triethylamine at - 60° to 23° is promoted by catalytic amounts of ditertiary 1,2-diamines. The regioselectivity depends
Ring opening of epoxides with carboxylates and phenoxides in micellar media catalyzed with Ce(OTf)4
Iranpoor,Firouzabadi,Safavi,Shekarriz
, p. 2287 - 2293 (2007/10/03)
Efficient ring opening reaction of epoxides with carboxylates and phenoxide anions catalyzed with ceric triflate is performed in micellar media. This new method is a useful procedure for the preparation of β-carboxy and phenoxy alcohols from epoxides under mild reaction conditions.
