Asymmetric Catalysis via Dynamic Kinetic Resolution

ChemInform ◽  
2007 ◽  
Vol 38 (29) ◽  
Author(s):  
Jan-E. Baeckvall
Keyword(s):  
Asymmetric Catalysis ◽  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution

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.

Recent Progress and Applications of Transition-Metal-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution

Synthesis ◽  
2020 ◽  
Vol 53 (01) ◽  
pp. 30-50
Author(s):  
Phannarath Phansavath ◽  
Virginie Ratovelomanana-Vidal ◽  
Ricardo Molina Betancourt ◽  
Pierre-Georges Echeverria ◽  
Tahar Ayad
Keyword(s):  
Transition Metal ◽  
Asymmetric Catalysis ◽  
Kinetic Resolution ◽  
Asymmetric Hydrogenation ◽  
Short Review ◽  
Transfer Hydrogenation ◽  
Dynamic Kinetic Resolution ◽  
Catalytic Systems ◽  
Keto Esters ◽  
Metal Catalyzed

AbstractBased on the ever-increasing demand for enantiomerically pure compounds, the development of efficient, atom-economical, and sustainable methods to produce chiral alcohols and amines is a major concern. Homogeneous asymmetric catalysis with transition-metal complexes including asymmetric hydrogenation (AH) and transfer hydrogenation (ATH) of ketones and imines through dynamic kinetic resolution (DKR) allowing the construction of up to three stereogenic centers is the main focus of the present short review, emphasizing the development of new catalytic systems combined to new classes of substrates and their applications as well.1 Introduction2 Asymmetric Hydrogenation via Dynamic Kinetic Resolution2.1 α-Substituted Ketones2.2 α-Substituted β-Keto Esters and Amides2.3 α-Substituted Esters2.4 Imine Derivatives3 Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution3.1 α-Substituted Ketones3.2 α-Substituted β-Keto Esters, Amides, and Sulfonamides3.3 α,β-Disubstituted Cyclic Ketones3.4 β-Substituted Ketones3.5 Imine Derivatives4. Conclusion

scholarly journals Metal-free oxidative cross-coupling enabled practical synthesis of atropisomeric QUINOL and its derivatives

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Peng-Ying Jiang ◽  
Kai-Fang Fan ◽  
Shaoyu Li ◽  
Shao-Hua Xiang ◽  
Bin Tan
Keyword(s):  
Asymmetric Catalysis ◽  
Kinetic Resolution ◽  
Academic Research ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Industrial Applications ◽  
Lewis Base ◽  
Production Costs ◽  
Metal Free ◽  
Base Catalysts

AbstractAs an important platform molecule, atropisomeric QUINOL plays a crucial role in the development of chiral ligands and catalysts in asymmetric catalysis. However, efficient approaches towards QUINOL remain scarce, and the resulting high production costs greatly impede the related academic research as well as downstream industrial applications. Here we report a direct oxidative cross-coupling reaction between isoquinolines and 2-naphthols, providing a straightforward and scalable route to acquire the privileged QUINOL scaffolds in a metal-free manner. Moreover, a NHC-catalyzed kinetic resolution of QUINOL N-oxides with high selectivity factor is established to access two types of promising axially chiral Lewis base catalysts in optically pure forms. The utility of this methodology is further illustrated by facile transformations of the products into QUINAP, an iconic ligand in asymmetric catalysis.

Development of a Robust and Highly Selective Ru(II)-Catalyzed Dynamic Kinetic Resolution Used to Manufacture AMG 232

2020 ◽  
Vol 24 (6) ◽  
pp. 1164-1174
Author(s):  
Austin G. Smith ◽  
Matthew M. Bio ◽  
John T. Colyer ◽  
Khalid Diker ◽  
Gilles Gorins ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution

Catalytic Atroposelective Dynamic Kinetic Resolution of Biaryl Lactones with Activated Isocyanides

2021 ◽  
Author(s):  
Linghui Qian ◽  
Ling-Fei Tao ◽  
Wen-Tao Wang ◽  
Ehtesham Jameel ◽  
Zhang-Hong Luo ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution

Efforts towards a Noyori reduction of a 3-fluorpiperidin-4-one with dynamic kinetic resolution

2021 ◽  
pp. 152764
Author(s):  
Jacques Le Paih ◽  
Dane A. Goff ◽  
Rajinder Singh ◽  
Simon J. Shaw
Keyword(s):  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution
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