In the hexahedral hydrocarbon cubane, replacing hydrogen with other atoms at three positions within any one of the internal tetrahedrons can conceptually lead to the formation of a unique class of chiral molecules. In pursuit of this endeavor, we prepared 1,3-dibromo-4-deuteriocubane-,-diisopropylcarboxamide, which upon treatment with zincates affords 1,3,5-trisubstituted cubanes via simultaneous two-position substitution reactions. The proposed chiral attributes of this stereogeometric class were confirmed by enantiomeric resolution of a -bromobenzyl derivative using chiral HPLC.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.0c01142 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Simplified Nomenclature and Projection Diagrams of Chiral Cubane Analogs.
ACS Omega
September 2024
Keck Graduate Institute, School of Pharmacy, 535 Watson Drive, Claremont, California 91711, United States.
A simplified nomenclature for chiral cubane analogs is proposed where analogs with a clockwise systematic continuous numbering of the cubane core are designated as ()-, and analogs with an anticlockwise continuous numbering of the cubane core are designated as ()-. This method is accurate, allows for the rapid conversion of the chemical name to a structure, and it eliminates the need to designate the stereochemistry of each of the 8 carbons of cubane.
View Article and Find Full Text PDFChiral Heterometallic CuLn Complexes with Enantiopure Schiff Base Ligands: Synthesis, Structural, Spectroscopic and Magnetic Studies.
Chempluschem
August 2024
Institute of Nanoscience and Nanotechnology, NCSR "Demokritos", 15310, Aghia Paraskevi, Athens, Greece.
The enantiomerically pure Schiff base ligands HL-S and HL-R yield chiral heterometallic dodecanuclear complexes of the form [CuLn(OH)(OMe)(OCBu)(L-S or L-R)(HO)] where Ln=Gd (1S), Tb (2S), Dy (3S, 3R), Ho (4S, 4R), Er (5S) or Y (6S, 6R) and HL=(S or R)-2-{[(1-hydroxypropan-2-yl)imino]methyl}-6-methoxyphenol. The complexes are isomorphous and crystallize in the non-centrosymmetric polar space group C2 in enantiomeric conformation. The chirality of the Schiff base ligands originates from the respective S- or R- enantiomer of 2-aminopropan-1-ol, is imparted to the complexes and to the crystals that belong to non-centrosymmetric space group.
View Article and Find Full Text PDFComputational Research on Ag(I)-Catalyzed Cubane Rearrangement: Mechanism, Metal and Counteranion Effect, Ligand Engineering, and Post-Transition-State Desymmetrization.
J Org Chem
March 2024
BSJ Institute, Haidian, Beijing 100084, People's Republic of China.
Ag(I) salts have demonstrated superior catalytic activity in the cubane-cuneane rearrangement. This research presents a comprehensive mechanistic investigation using high-level computations. The reaction proceeds via oxidative addition (OA) of Ag(I) to the C-C bond, followed by C-Ag bond cleavage and subsequent dynamically concerted carbocation rearrangement.
View Article and Find Full Text PDFSpectral Analysis on Cuba-Lumacaftor: Cubane as Benzene Bioisosteres of Lumacaftor.
ACS Omega
November 2023
Department of Central Sterile Supply, The First Affiliated Hospital of Jinzhou Medical University, Jinzhou, Liaoning 121004, China.
In this paper, we theoretically investigate the electronic structure and physical properties of cuba-lumacaftor, cubane as benzene bioisosteres of lumacaftor, stimulated by recent experimental reports [Wiesenfeldt M. P.; Nature2023, 618, 513-518].
View Article and Find Full Text PDFOne-Dimensional Chiral Copper Iodide Chain-Like Structure Cu I (R/S-3-quinuclidinol) with Near-Unity Photoluminescence Quantum Yield and Efficient Circularly Polarized Luminescence.
Small
June 2023
Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055, P. R. China.
Chiral organic-inorganic hybrid metal halide materials have shown great potential for circularly polarized luminescence (CPL) related applications for their tunable structures and efficient emissions. Here, this work combines the highly emissive Cu I cubane cluster with chiral organic ligand R/S-3-quinuclidinol, to construct a new type of 1D Cu-I chains, namely Cu I (R/S-3-quinuclidinol) , crystallizing in noncentrosymmetric monoclinic P2 space group. These enantiomorphic hybrids exhibit long-term stability and show bright yellow emission with a photoluminescence quantum yield (PLQY) close to 100%.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!