Pd(0)-catalyzed amination was employed for the synthesis of a new family of ()-1,1'-bianaphthalene-2,2'-diamine derivatives possessing additional chiral and fluorophore substituents. The compounds thus obtained were tested as potential detectors of seven amino alcohols, and some of them were found to be able to recognize individual enantiomers of certain amino alcohols by specific changes of their emission spectra in the presence of these analytes. A pronounced dependence of the detecting abilities on the nature of the substituents in the ()-BINAM derivatives was observed.
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http://dx.doi.org/10.3390/s20113234 | DOI Listing |
The [5,5]-sigmatropic rearrangement is a less-studied reaction and may be strategically utilized to devise unique synthetic processes. Herein, we document a diboron-enabled [5,5]-sigmatropic rearrangement for practical synthesis of BINAM derivatives. Mechanistically, a concerted activation of azonaphthalenes by diboron creates a unique ten-membered transition state, which subsequently triggers a [5,5]-sigmatropic rearrangement.
View Article and Find Full Text PDFInt J Mol Sci
July 2024
School of Chemical Engineering, Sichuan University, Chengdu 610207, China.
Lysine plays a crucial role in promoting development, enhancing immune function, and improving the function of central nervous system tissues. The two configurational isomers of amino acids have significantly different effects. Currently, methods for chiral recognition of lysine have been reported; however, previous detection methods have drawbacks such as expensive equipment and complicated detection processes.
View Article and Find Full Text PDFOrg Biomol Chem
May 2024
Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo, Japan.
1,1'-Binaphthyl-2,2'-diamine (BINAM) is a useful axially chiral compound. The kinetic resolution of BINAM is one of the most crucial methods for synthesizing chiral BINAM. We have developed a chiral calcium phosphate-catalyzed kinetic resolution of BINAM by utilizing an acylation reaction to produce a mono-amide.
View Article and Find Full Text PDFJACS Au
February 2024
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, China.
Atropisomeric biaryls have found crucial applications in versatile chiral catalysts as well as in ligands for transition metals. Herein, we have developed an efficient crystallization-induced deracemization (CID) method to access chiral biaryls from their racemates with a chiral ammonium salt under copper catalysis including BINOL, NOBIN, and BINAM derivatives. After being significantly accelerated by its bidentate diamine ligand, the copper catalyst exhibits high efficiency and selectivity in racemizing biaryl skeletons, and the cocrystal complex would be enantioselectively formed together with chiral ammonium salt, which on acid-quenching would directly deliver chiral biaryl without further chromatographic purification.
View Article and Find Full Text PDFNat Commun
August 2022
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai, 200237, China.
Molecular conformations induced by the rotation about single bonds play a crucial role in chemical transformations. Revealing the relationship between the conformations of chiral catalysts and the enantiodiscrimination is a formidable challenge due to the great difficulty in isolating the conformers. Herein, we report a chiral catalytic system composed of an achiral catalytically active unit and an axially chiral 1,1'-bi-2-naphthol (BINOL) unit which are connected via a C-O single bond.
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