75024-00-9Relevant academic research and scientific papers
Metal-Free and User-Friendly Regioselective Hydroxyfluorination of Olefins
Sedgwick, Daniel M.,López, Inés,Román, Raquel,Kobayashi, Nanako,Okoromoba, Otome E.,Xu, Bo,Hammond, Gerald B.,Barrio, Pablo,Fustero, Santos
supporting information, p. 2338 - 2341 (2018/04/30)
A simple, user-friendly, metal-free protocol for the regioselective anti-Markovnikov hydrofluorination of olefins using readily available and inexpensive reagents has been developed. This new approach displays a broader scope than previously reported methodologies and has been applied to the late-stage fluorination of a complex molecule, giving rise to a fluorosteroid derivative. The stereochemistry of the process has also been studied in some detail.
Influence of Alcohol β-Fluorination on Hydrogen-Bond Acidity of Conformationally Flexible Substrates
Graton, Jerome,Compain, Guillaume,Besseau, Francois,Bogdan, Elena,Watts, Joseph M.,Mtashobya, Lewis,Wang, Zhong,Weymouth-Wilson, Alex,Galland, Nicolas,Le Questel, Jean-Yves,Linclau, Bruno
supporting information, p. 2811 - 2819 (2017/03/05)
Rational modulations of molecular interactions are of significant importance in compound properties optimization. We have previously shown that fluorination of conformationally rigid cyclohexanols leads to attenuation of their hydrogen-bond (H-bond) donat
Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols
Kolodiazhna, Olga O.,Kolodiazhna, Anastasy O.,Kolodiazhnyi, Oleg I.
, p. 37 - 42 (2013/02/25)
The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation.
Conformational analysis of cis-2-halocyclohexanols; Solvent effects by NMR and theoretical calculations
Basso, Ernani A.,Abiko, Layara A.,Gauze, Gisele F.,Pontes, Rodrigo M.
experimental part, p. 145 - 153 (2011/03/19)
Conformational problems often involve very small energy differences, even low as 0.5 kcal mol-1. This accuracy can be achieved by theoretical methods in the gas phase with the appropriate accounting of electron correlation. The solution behavio
Fluorinated ε-caprolactone: Synthesis and ring-opening polymerization of new α-fluoro-ε-caprolactone monomer
Al-Azemi, Talal F.,Mohamod, Abdirahman A.
experimental part, p. 5431 - 5438 (2012/05/20)
Fluorinated polyester was synthesized from a novel α-fluoro-ε- caprolactone monomer (α-FCL). The monomer was synthesized from commercially available cyclohexene oxide in three steps. Baeyer-Villiger reaction using 3-chloroperoxybenzoic acid of the corresp
Asymmetric hydrogenation of racemic 2-fluorocyclohexanone over cinchona modified Pt/Al2O3 catalyst
Szori, Kornel,Szoellosi, Gyoergy,Bartok, Mihaly
, p. 255 - 259 (2007/10/03)
The first example of enantioselective heterogeneous catalytic hydrogenation of an α-fluoro ketone is reported. The hydrogenation of racemic 2-fluorocyclohexanone over cinchonidine- or methoxycinchonidine-modified Pt/Al2O3 resulted in
Trifluoromethylthiocopper catalyzed oxirane ring opening
Munavalli,Rohrbaugh,Durst
, p. 1657 - 1671 (2007/10/03)
Trifluoromethylthiocopper has been found to catalyze the opening of the epoxide ring and to furnish not-so-easily accessible novel trifluoromethylthiolated α-hydroxy compounds. This communication presents the mechanism of the formation of the various comp
Regioselective synthesis of fluorohydrines via SN2-type ring-opening of epoxides with TBABF-KHF2
Akiyama, Yuriko,Fukuhara, Tsuyoshi,Hara, Shoji
, p. 1530 - 1532 (2007/10/03)
We found that the ring-opening fluorination of terminal epoxides using TBABF-KHF2 proceeds with high selectivity through the SN2 mechanism. As TBABF-KHF2 is easily obtainable, is stable, and can be used in glassware, it ca
Synthesis of optically active vicinal fluorohydrins by lipase-catalyzed deracemization
Woelker, Doerthe,Haufe, Guenter
, p. 3015 - 3021 (2007/10/03)
Three microbial lipases have been used to deracemize trans-2-fluorocycloalkanols 2 both by hydrolysis of the corresponding acetates 3 or chloroacetates 4 and by esterification of the fluorohydrins 2 using vinyl acetate and vinyl chloroacetate, respectivel
