Enantioselective Syntheses of Axially Chiral Phosphonates or Phosphine Oxides via Asymmetric Suzuki Reactions with Chiral Sulfinamide Monophosphine Ligands

2019 ◽  
Vol 4 (17) ◽  
pp. 5122-5125 ◽  
Author(s):  
Yaqi Zhang ◽  
Yongsu Li ◽  
Bendu Pan ◽  
Hao Xu ◽  
Hao Liang ◽  
...  
Keyword(s):  
Phosphine Oxides ◽  
Suzuki Reactions ◽  
Axially Chiral ◽  
Enantioselective Syntheses

Catalytic Atroposelective Dynamic Kinetic Resolution of Substituted Indoles

Synlett ◽  
2021 ◽  
Author(s):  
Ahreum Kim ◽  
Yongseok Kwon
Keyword(s):  
Asymmetric Catalysis ◽  
Kinetic Resolution ◽  
Ortho Position ◽  
Dynamic Kinetic Resolution ◽  
Research Attention ◽  
Considerable Research ◽  
Chiral Phosphoric Acid ◽  
Axially Chiral ◽  
High Yields ◽  
Enantioselective Syntheses

Advances in asymmetric catalysis have led to enormous progress in the atroposelective synthesis of axially chiral biaryls. Because of the biological importance of indoles, stereogenic axes in aryl-substituted indoles have attracted considerable research attention in recent years. Here we present a summary of recent advances in the atroposelective synthesis of aryl-substituted indoles by dynamic kinetic resolution. While several researchers have developed enantioselective syntheses of 3-arylindoles, N-arylindoles have been much less studied. Accordingly, we have reported a Pictet–Spengler reaction with catalytic and enantioselective control of the axial chirality around the C−N bond of the product. A chiral phosphoric acid induces the cyclization smoothly and with high yields and excellent enantioselectivities. To achieve this high selectivity, an NH group at the ortho position of the N-substituted aromatic ring that interacts favorably with the catalyst is required. Furthermore, when substituted aldehydes are used instead of paraformaldehyde, both the point and axial chiralities can be controlled during the cyclization.

Asymmetric C–H Activation for the Synthesis of P- and Axially Chiral Biaryl Phosphine Oxides by an Achiral Cp*Ir Catalyst with Chiral Carboxylic Amide

ACS Catalysis ◽  
2021 ◽  
pp. 193-199
Author(s):  
Chao-Wei Zhang ◽  
Xian-Qi Hu ◽  
Yuan-Hao Dai ◽  
Peng Yin ◽  
Chuanyong Wang ◽  
...  
Keyword(s):  
Phosphine Oxides ◽  
Axially Chiral

scholarly journals Access to P - and Axially Chiral Biaryl Phosphine Oxides by Enantioselective Cpx IrIII -Catalyzed C−H Arylations

2018 ◽  
Vol 57 (39) ◽  
pp. 12901-12905 ◽  
Author(s):  
Yun-Suk Jang ◽  
Łukasz Woźniak ◽  
Julia Pedroni ◽  
Nicolai Cramer
Keyword(s):  
Phosphine Oxides ◽  
Axially Chiral

Access to P - and Axially Chiral Biaryl Phosphine Oxides by Enantioselective Cpx IrIII -Catalyzed C−H Arylations

2018 ◽  
Vol 130 (39) ◽  
pp. 13083-13087 ◽  
Author(s):  
Yun-Suk Jang ◽  
Łukasz Woźniak ◽  
Julia Pedroni ◽  
Nicolai Cramer
Keyword(s):  
Phosphine Oxides ◽  
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>

Synthesis and Solid-State Structure of (4-Hydroxy-3,5-diiodophenyl)phosphine Oxides. Dimeric Motifs with the Assistance of O-H···O=P Hydrogen Bonds

2015 ◽  
Vol 19 (5) ◽  
pp. 469-474 ◽  
Author(s):  
Nicholas Bewick ◽  
Agata Arendt ◽  
Yan Li ◽  
S.awomir Szafert ◽  
Tadeusz Lis ◽  
...  
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Phosphine Oxides ◽  
State Structure ◽  
Solid State Structure
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