1115-39-5Relevant academic research and scientific papers
Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides
Paz, Nieves R.,Rodríguez-Sosa, Dionisio,Valdés, Haydee,Marticorena, Ricardo,Melián, Daniel,Copano, M. Belén,González, Concepción C.,Herrera, Antonio J.
supporting information, p. 2370 - 2373 (2015/06/02)
Mechanistic evidence observed in Hofmann-L?ffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity. (Chemical Equation Presented).
Design, synthesis, and applications of potential substitutes of t-Bu-phosphinooxazoline in Pd-catalyzed asymmetric transformations and their use for the improvement of the enantioselectivity in the Pd-catalyzed allylation reaction of fluorinated allyl enol carbonates
Belanger, Etienne,Pouliot, Marie-France,Courtemanche, Marc-Andre,Paquin, Jean-Francois
, p. 317 - 331 (2012/02/15)
The design, synthesis, and applications of potential substitutes of t-Bu-PHOX in asymmetric catalysis is reported. The design relies on the incorporation of geminal substituents at C5 in combination with a substituent at C4 other than t-butyl (i-Pr, i-Bu, or s-Bu). Most of these new members of the PHOX ligand family behave similarly in terms of stereoinduction to t-Bu-PHOX in three palladium-catalyzed asymmetric transformations. Electronically modified ligands were also prepared and used to improve the enantioselectivity in the Pd-catalyzed allylation reaction of fluorinated allyl enol carbonates.
Kinetic resolution of protected α-amino acid derivatives by a chiral O-nucleophilic acyl transfer catalyst
Notte, Gregory T.,Sammakia, Tarek
, p. 4230 - 4231 (2007/10/03)
The kinetic resolution of α-trifluoroacetamido N-acyl oxazolidinethiones using 5-10% of the chiral, nonracemic O-nucleophilic acyl transfer catalyst 2 is described. A variety of substrates participate in this reaction in excellent yields, with s-factors ranging from 20 to 86. Copyright
Chiral Discrimination in the Liquid Phase: Excess Volumes of Binary Mixtures of Amino Acid Derivatives
Lepori, Luciano,Koppenhoefer, Beenhard
, p. 6862 - 6864 (2007/10/02)
Volume changes on mixing the enantiomers of N-trifluoroacetylamino acid methyl esters (N-TFA-amino acid-OMe) were determined at 25 deg C by means of a high-precision vibrating-tube densimeter.The excess molar volume (VE) for the racemic mixtures of N-TFA-Ala-OMe 1, N-TFA-Val-OMe 2, and N-TFA-Leu-OMe 3, were found as VE = 0.0098, -0.0458, and 0.035 cm3 mol-1, respectively.For 2 and 3, these volumetric effects of discriminating interactions between enantiomers in the liquid phase are the largest ever observed.
