Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Several convergent techniques were used to characterize 1,1'-bi-2-naphthol (BINOL) and some of its properties. Its acidity in the gas-phase, from neutral species to monoanion, was measured by mass spectrometry. The conformation and structure of BINOL in the gas phase was determined by microwave rotational spectroscopy. NMR experiments in fluorosulfonic acid established that BINOL was monoprotonated on one of the hydroxyl oxygen atoms. The enantiomerization barriers reported in the literature for BINOL under neutral, basic, and acid conditions were analyzed with regard to the species involved. Finally, DFT calculations allowed all of these results to be gathered in a coherent picture of the BINOL structure.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.201402686 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units.
Beilstein J Org Chem
August 2025
Faculty of Chemistry (Organic Chemistry) and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, 45141 Essen, Germany.
Chiral macrocycles hold significant importance in various scientific fields due to their unique structural and chemical properties. By controlling their size, shape, and substituents, chiral macrocycles offer a platform for designing and synthesizing highly efficient catalysts, chemosensors, and functional materials. We have recently made strides in developing macrocyclic organocatalysts; however, their synthesis remains challenging.
View Article and Find Full Text PDFChiral Amino Alcohols via Catalytic Enantioselective Petasis Borono-Mannich Reactions.
J Org Chem
August 2025
Department of Chemistry and Center for Molecular Discovery (BU-CMD), Life Sciences and Engineering Building, Boston University, 24 Cummington Mall, Boston, Massachusetts 02215, United States.
Chiral amino alcohols are valuable building blocks in the synthesis of drugs, natural products, and chiral ligands used in enantioselective catalysis. The Petasis borono-Mannich reaction is a multicomponent condensation reaction of aldehydes, amines, and boronic acids to afford chiral amines. This report describes a practical, easily scaled, enantioselective Petasis borono-Mannich reaction of glycolaldehyde with primary or secondary amines and boronates catalyzed by BINOL-derived catalysts to afford chiral 1,2-amino alcohols in high yields and enantioselectivities.
View Article and Find Full Text PDFCatalytic Enantioselective Aza-Friedel-Crafts Reaction of Ketimines and Indoles for Constructing Tetrasubstituted Carbon Centers Adjacent to Two Heteroatoms.
J Org Chem
August 2025
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu 610106, China.
A highly enantioselective aza-Friedel-Crafts reaction of benzothiophene-2,3-dione-derived ketimines and indoles catalyzed by BINOL-derived chiral phosphoric acid was developed for the first time. This protocol enabled the synthesis of structurally diverse enantiopure hybrid 3-indolylmethanamine-benzothiophenes featuring a chiral quaternary carbon center adjacent to both N and S atoms, achieving high yields and high to excellent enantioselectivities (up to 99% yield and 99% ee). The reaction exhibits broad substrate scope, high reactivity, simple operation, and mild conditions.
View Article and Find Full Text PDFMethyl itaconate-anthracene adducts (MIAs) facilitate the enantiomeric separation of 1,1'-bi-2-naphthols thin-layer chromatography (TLC) with trends predicted by molecular dynamics simulations.
RSC Adv
August 2025
Department of Chemistry, Faculty of Science, Chiang Mai University 239 Huay Kaew Road Chiang Mai 50200 Thailand
1,1'-bi-2-naphthols (BINOLs) and their derivatives have been extensively studied over the years. Enantiopure BINOLs are crucial in asymmetric synthesis, circularly polarized luminescent dyes, and charge transfer host systems. Several methods, including asymmetric oxidative coupling, enzymatic resolution, and chemical resolution, have been explored to prepare enantiopure BINOLs.
View Article and Find Full Text PDFIridium-Lewis Acid Bifunctional Catalyst-Enabled Regio- and Enantioselective C(sp)-H -Borylation of α,α-Diarylcarboxamides.
J Am Chem Soc
August 2025
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur 741246, India.
Enantioselective C(sp)-H activation typically relies on forming rigid 5- or 6-membered metallacyclic intermediates. Examples involving direct metalation at remote C(sp)-H bonds, which require larger metallacycles, remain scarce. Herein, we report a series of 1,1'-bi-2-naphthol (BINOL)-derived chiral bipyridine ligands that enable iridium-catalyzed regio- and enantioselective -borylation of α,α-diarylcarboxamides, generating an all-carbon quaternary stereocenter in high yields and excellent regio- and enantioselectivities.
View Article and Find Full Text PDF