scholarly journals Chiral Counterion Strategy in Cu-Catalyzed Asymmetric Allylic Oxidation of Linear Alkenes

2015 ◽  
Vol 2 (1) ◽  
Author(s):  
Celia A. Incerti-Pradillos ◽  
Daniel Hudson ◽  
Andrei V. Malkov
Keyword(s):  
Allylic Oxidation ◽  
Counter Ion ◽  
Axially Chiral ◽  
Phosphoric Acids

Abstract Application of a chiral counter-ion strategy in the Kharasch-Sosnovsky reaction is reported. Copper(I) phosphates obtained from axially chiral, BINOL-derived phosphoric acids were investigated as catalysts in the enantioselective allylic oxidation of acyclic alkenes. Good yields and high regioselectivity towards branched allylic ester have been achieved. The chiral phosphates investigated exhibited modest enantioselectivities.

ChemInform Abstract: Synthesis, Characterization and Application of Some Axially Chiral Binaphthyl Phosphoric Acids in Asymmetric Mannich Reaction.

ChemInform ◽  
2015 ◽  
Vol 46 (39) ◽  
pp. no-no
Author(s):  
Yuanyong Yao ◽  
Hua Shu ◽  
Bangcheng Tang ◽  
Shixue Chen ◽  
Zhongying Lu ◽  
...  
Keyword(s):  
Mannich Reaction ◽  
Axially Chiral ◽  
Phosphoric Acids

Synthesis, Characterization and Application of Some Axially Chiral Binaphthyl Phosphoric Acids in Asymmetric Mannich Reaction

2015 ◽  
Vol 33 (5) ◽  
pp. 601-609 ◽  
Author(s):  
Yuanyong Yao ◽  
Hua Shu ◽  
Bangcheng Tang ◽  
Shixue Chen ◽  
Zhongying Lu ◽  
...  
Keyword(s):  
Mannich Reaction ◽  
Axially Chiral ◽  
Phosphoric Acids

The Temperature and Counter-ion Dependency of Cation Exchange Equilibria

1960 ◽  
Vol 25 (1_2) ◽  
pp. 81-89 ◽  
Author(s):  
O. D. Bonner ◽  
G. Dickel ◽  
H. Brümmer
Keyword(s):  
Cation Exchange ◽  
Counter Ion

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>

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