Inherently Chiral Calix[5]arenes Incorporating an Axially Chiral Binaphthyl Moiety: Synthesis, Structures and Chiral Recognition

2014 ◽  
Vol 2015 (4) ◽  
pp. 765-774 ◽  
Author(s):  
Wen-Zhen Zhang ◽  
Ke Yang ◽  
Si-Zhe Li ◽  
Hui Ma ◽  
Jun Luo ◽  
...  
Keyword(s):  
Chiral Recognition ◽  
Axially Chiral ◽  
Inherently Chiral

Deracemization of an axially chiral biphenylic derivative as a tool for investigating chiral recognition in self-assemblies

Chirality ◽  
2003 ◽  
Vol 15 (5) ◽  
pp. 441-447 ◽  
Author(s):  
Stefano Borocci ◽  
Francesca Ceccacci ◽  
Luciano Galantini ◽  
Giovanna Mancini ◽  
Donato Monti ◽  
...  
Keyword(s):  
Chiral Recognition ◽  
Axially Chiral

Inherently Chiral Resorcin[4]arenes with Urea and Amide Side Arms: Synthesis, Structure and Chiral Recognition

2013 ◽  
Vol 2013 (7) ◽  
pp. 1240-1245 ◽  
Author(s):  
Sebastian Wiegmann ◽  
Gaku Fukuhara ◽  
Beate Neumann ◽  
Hans-Georg Stammler ◽  
Yoshihisa Inoue ◽  
...  
Keyword(s):  
Chiral Recognition ◽  
Inherently Chiral

scholarly journals Synthesis of upper rim-double-bridged calix[4]arenes bearing seven membered rings and related compounds

RSC Advances ◽  
2019 ◽  
Vol 9 (38) ◽  
pp. 22017-22030 ◽  
Author(s):  
M. Tlustý ◽  
V. Eigner ◽  
M. Babor ◽  
M. Kohout ◽  
P. Lhoták
Keyword(s):  
Chiral Recognition ◽  
Inherently Chiral ◽  
Upper Rim ◽  
Related Compounds

Calix[4]arenes bearing one or two bridges on the upper rim were prepared as novel inherently chiral derivatives potentially capable of chiral recognition.

Stereoselective Encapsulation for a Triarylmethylium o,o-Dimer by Natural γ-Cyclodextrin: Origin of Chiral Recognition for the Axially Chiral Dicationic Guest

Heterocycles ◽  
2017 ◽  
Vol 94 (6) ◽  
pp. 1123 ◽  
Author(s):  
Takanori Suzuki ◽  
Horacio Pérez-Sánchez ◽  
José P. Cerón-Carrasco ◽  
Hitomi Tamaoki ◽  
Yusuke Ishigaki ◽  
...  
Keyword(s):  
Chiral Recognition ◽  
Axially Chiral

Total Synthesis of Axially-Chiral Cannabinols: A New Platform for Cannabinoid-Based Drug Discovery

2019 ◽  
Author(s):  
Primali Navaratne ◽  
Jenny Wilkerson ◽  
Kavindri Ranasinghe ◽  
Evgeniya Semenova ◽  
Lance McMahon ◽  
...  
Keyword(s):  
Drug Discovery ◽  
Total Synthesis ◽  
Ground State ◽  
Chemical Space ◽  
Modern Medicine ◽  
The Novel ◽  
Pharmaceutical Development ◽  
Bioactive Component ◽  
Axially Chiral ◽  
New Directions

<div> <div> <div> <p>Phytocannabinoids, molecules isolated from cannabis, are gaining attention as promising leads in modern medicine, including pain management. Considering the urgent need for combating the opioid crisis, new directions for the design of cannabinoid-inspired analgesics are of immediate interest. In this regard, we have hypothesized that axially-chiral-cannabinols (ax-CBNs), unnatural (and unknown) isomers of cannabinol (CBN) may be valuable scaffolds for cannabinoid-inspired drug discovery. There are multiple reasons for thinking this: (a) ax-CBNs would have ground-state three-dimensionality akin to THC, a key bioactive component of cannabis, (b) ax-CBNs at their core structure are biaryl molecules, generally attractive platforms for pharmaceutical development due to their ease of functionalization and stability, and (c) atropisomerism with respect to phytocannabinoids is unexplored “chemical space.” Herein we report a scalable total synthesis of ax-CBNs, examine physical properties experimentally and computationally, and provide preliminary behavioral and analgesic analysis of the novel scaffolds. </p> </div> </div> </div>

Synthesis of Axially Chiral 2,2’-Bisphosphobiarenes via a Nickel-Catalyzed Asymmetric Ullmann Coupling: General Access to Privileged Chiral Ligands without Optical Resolution

2020 ◽  
Author(s):  
Ziqing Zuo ◽  
Raphael Kim ◽  
Donald Watson
Keyword(s):  
Optical Resolution ◽  
Chiral Ligands ◽  
Chiral Auxiliaries ◽  
Axially Chiral ◽  
Ullmann Coupling

<div><p>We report an asymmetric Ullmann-type homocoupling of <i>ortho-</i>(iodo)arylphosphine oxides and <i>ortho</i>-(iodo)arylphosphonates that results in highly enantioenriched axially chiral bisphosphine oxides and bisphosphonates in good yields and excellent enantioselectivities. These products are readily converted to enantioenriched biaryl bisphosphines without need for chiral auxiliaries or optical resolution. This process provides a straightforward and practical route for the development of previously uninvestigated atroposelective biaryl bisphosphine ligands.</p></div>

Enantioselective Recognition of Chiral Guests by the Water-Soluble Chiral Keplerate {Mo132} Spherical Capsule with 30 Inner Lactate Ligands

2019 ◽  
Author(s):  
Nancy Watfa ◽  
Weimin Xuan ◽  
Zoe Sinclair ◽  
Robert Pow ◽  
Yousef Abul-Haija ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Chiral Recognition ◽  
Association Constants ◽  
Water Soluble ◽  
Enantioselective Recognition ◽  
H Nmr ◽  
Dosy Nmr ◽  
Spherical Capsule ◽  
Surface Pores ◽  
Guest Chemistry

Investigations of chiral host guest chemistry are important to explore recognition in confined environments. Here, by synthesizing water-soluble chiral porous nanocapsule based on the inorganic metal-oxo Keplerate-type cluster, {Mo<sub>132</sub>} with chiral lactate ligands with the composition [Mo<sub>132</sub>O<sub>372</sub>(H<sub>2</sub>O)<sub>72</sub>(<i>x-</i>Lactate)<sub>30</sub>]<sup>42-</sup> (<i>x</i> = D or L), it was possible to study the interaction with a chiral guest, L/D-carnitine and (<i>R</i>/<i>S</i>)-2-butanol in aqueous solution. The enantioselective recognition was studied by quantitative <sup>1</sup>H NMR and <sup>1</sup>H DOSY NMR which highlighted that the chiral recognition is regulated by two distinct sites. Differences in the association constants (K) of L- and D-carnitine, which, due to their charge, are generally restricted from entering the interior of the host, are observed, indicating that their recognition predominantly occurs at the surface pores of the structure. Conversely, a larger difference in association constants (K<i><sub>S</sub></i>/K<i><sub>R</sub></i> = 3) is observed for recognition within the capsule interior of (<i>R</i>)- and (<i>S</i>)-2-butanol.

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