Oxazaborolidine-catalyzed reductive parallel kinetic resolution of ketones from β-nitro-azabicycles for the synthesis of chiral hypoestestatins 1, 2

2021 ◽  
Author(s):  
Wannaporn Disadee ◽  
Somsak Ruchirawat
Keyword(s):  
Kinetic Resolution ◽  
Novel Approach ◽  
Parallel Kinetic Resolution ◽  
Key Features

A novel approach for the synthesis of 13a-methyl tylophora alkaloids has been reported. The key features included two different synthetic pathways targeted at transforming the β-nitro-azabicycle to the phenanthrene core....

Probing the Parallel Kinetic Resolution of Racemic Oxazolidinones using Quasi-enantiomeric Profens

2006 ◽  
Author(s):  
Jason Eames ◽  
Gregory Coumbarides ◽  
Marco Dingjan ◽  
Tony Flinn ◽  
Northern Northen ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Parallel Kinetic Resolution

Catalytic Asymmetric Transformations of Racemic Aziridines

Synthesis ◽  
2020 ◽  
Vol 52 (12) ◽  
pp. 1738-1750 ◽  
Author(s):  
Zhuo Chai
Keyword(s):  
Ring Opening ◽  
Kinetic Resolution ◽  
Short Review ◽  
Asymmetric Transformations ◽  
Parallel Kinetic Resolution ◽  
Donor Acceptor ◽  
Molecular Architectures ◽  
Catalytic Asymmetric ◽  
Asymmetric Transformation ◽  
Asymmetric Ring Opening

The catalytic asymmetric ring-opening transformations of aziridines represent an important strategy for the construction of various chiral nitrogen-containing molecular architectures. This short review covers the progress achieved in the catalytic asymmetric transformation of racemic aziridines, focusing on the catalytic strategies employed for each different type of such aziridines.1 Introduction2 Reaction of Racemic 2-Vinylaziridines3 Reaction of Racemic 2-Alkylaziridines3.1 Regiodivergent Parallel Kinetic Resolution3.2 Kinetic Resolution4 Reaction of Racemic 2-(Hetero)arylaziridines4.1 Kinetic Resolution4.2 Enantioconvergent Transformation5 Reaction of Racemic Donor–Acceptor-Type Aziridines6 Conclusion and Outlook

Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Phthaloyl and N-Naphthaloyl (S)-Amino Acyl Chlorides: Possibility of Parallel Kinetic Resolution

2018 ◽  
Vol 483 (2) ◽  
pp. 293-296
Author(s):  
D. A. Gruzdev ◽  
E. N. Chulakov ◽  
L. Sh. Sadretdinova ◽  
G. L. Levit ◽  
V. P. Krasnov ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Heterocyclic Amines ◽  
Acyl Chlorides ◽  
Parallel Kinetic Resolution

scholarly journals Parallel Interconnected Kinetic Asymmetric Transformation (PIKAT) with an Immobilized ω-Transaminase in Neat Organic Solvent

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2140 ◽  
Author(s):  
Wesley Böhmer ◽  
Lucien Koenekoop ◽  
Timothée Simon ◽  
Francesco G. Mutti
Keyword(s):  
Kinetic Resolution ◽  
Enantiomeric Excess ◽  
Molar Ratio ◽  
Chiral Amines ◽  
Aqueous Environment ◽  
Chiral Amine ◽  
Parallel Kinetic Resolution ◽  
Pharmaceutical Manufacture ◽  
Prochiral Ketones ◽  
Asymmetric Transformation

Comprising approximately 40% of the commercially available optically active drugs, α-chiral amines are pivotal for pharmaceutical manufacture. In this context, the enzymatic asymmetric amination of ketones represents a more sustainable alternative than traditional chemical procedures for chiral amine synthesis. Notable advantages are higher atom-economy and selectivity, shorter synthesis routes, milder reaction conditions and the elimination of toxic catalysts. A parallel interconnected kinetic asymmetric transformation (PIKAT) is a cascade in which one or two enzymes use the same cofactor to convert two reagents into more useful products. Herein, we describe a PIKAT catalyzed by an immobilized ω-transaminase (ωTA) in neat toluene, which concurrently combines an asymmetric transamination of a ketone with an anti-parallel kinetic resolution of an amine racemate. The applicability of the PIKAT was tested on a set of prochiral ketones and racemic α-chiral amines in a 1:2 molar ratio, which yielded elevated conversions (up to >99%) and enantiomeric excess (ee, up to >99%) for the desired products. The progress of the conversion and ee was also monitored in a selected case. This is the first report of a PIKAT using an immobilized ωTA in a non-aqueous environment.

Enzymatic Parallel Kinetic Resolution of Mixtures ofd/l2′-Deoxy and Ribonucleosides: An Approach for the Isolation of β-l-Nucleosides†

2010 ◽  
Vol 75 (19) ◽  
pp. 6605-6613 ◽  
Author(s):  
Saúl Martínez-Montero ◽  
Susana Fernández ◽  
Yogesh S. Sanghvi ◽  
Vicente Gotor ◽  
Miguel Ferrero
Keyword(s):  
Kinetic Resolution ◽  
Parallel Kinetic Resolution
Sign in / Sign up

Export Citation Format

Share Document