Non-enzymatic acylative kinetic resolution of primary allylic amines

2013 ◽  
Vol 49 (81) ◽  
pp. 9338 ◽  
Author(s):  
Amandine Kolleth ◽  
Martin Cattoen ◽  
Stellios Arseniyadis ◽  
Janine Cossy
Keyword(s):  
Kinetic Resolution ◽  
Allylic Amines

ChemInform Abstract: A Dual-Catalysis/Anion-Binding Approach to the Kinetic Resolution of Allylic Amines.

ChemInform ◽  
2011 ◽  
Vol 42 (36) ◽  
pp. no-no
Author(s):  
Eric G. Klauber ◽  
Nisha Mittal ◽  
Tejas K. Shah ◽  
Daniel Seidel
Keyword(s):  
Kinetic Resolution ◽  
Anion Binding ◽  
Allylic Amines ◽  
Dual Catalysis

ChemInform Abstract: Non-enzymatic Acylative Kinetic Resolution of Primary Allylic Amines.

ChemInform ◽  
2014 ◽  
Vol 45 (7) ◽  
pp. no-no
Author(s):  
Amandine Kolleth ◽  
Martin Cattoen ◽  
Stellios Arseniyadis ◽  
Janine Cossy
Keyword(s):  
Kinetic Resolution ◽  
Allylic Amines

A Dual-Catalysis/Anion-Binding Approach to the Kinetic Resolution of Allylic Amines

2011 ◽  
Vol 13 (9) ◽  
pp. 2464-2467 ◽  
Author(s):  
Eric G. Klauber ◽  
Nisha Mittal ◽  
Tejas K. Shah ◽  
Daniel Seidel
Keyword(s):  
Kinetic Resolution ◽  
Anion Binding ◽  
Allylic Amines ◽  
Dual Catalysis

Kinetic resolution of primary allylic amines via palladium-catalyzed asymmetric allylic alkylation of malononitriles

2015 ◽  
Vol 13 (19) ◽  
pp. 5367-5371 ◽  
Author(s):  
Yong Wang ◽  
Ya-Nan Xu ◽  
Guo-Sheng Fang ◽  
Hong-Jian Kang ◽  
Yonghong Gu ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Bond Cleavage ◽  
Allylic Alkylation ◽  
Allylic Amines ◽  
Asymmetric Allylic Alkylation ◽  
New Strategy ◽  
Palladium Catalyzed

A new strategy has been developed for the catalytic kinetic resolution of primary allylic amines via enantioselective C–N bond cleavage.

Synthesis of B-ring-fluorinated (−)-epicatechin gallate derivatives

2020 ◽  
Vol 18 (21) ◽  
pp. 4024-4028
Author(s):  
David D. S. Thieltges ◽  
Kai D. Baumgarten ◽  
Carina S. Michaelis ◽  
Constantin Czekelius
Keyword(s):  
Kinetic Resolution ◽  
Convergent Sequence ◽  
Epicatechin Gallate

Electronically modified, fluorinated catechins and epicatechins are enantioselectively synthesized in a short, convergent sequence via kinetic resolution.

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

Catalyst- and Silane- Controlled Enantioselective Hydrofunctionalization of Alkenes by Cobalt-Catalyzed Hydrogen Atom Transfer and Radical-Polar Crossover

2020 ◽  
Author(s):  
Kousuke Ebisawa ◽  
Kana Izumi ◽  
Yuka Ooka ◽  
Hiroaki Kato ◽  
Sayori Kanazawa ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Absolute Configuration ◽  
Kinetic Resolution ◽  
Hydrogen Atom Transfer ◽  
Biologically Active ◽  
Atom Transfer ◽  
High Concentration ◽  
Chain Reaction ◽  
Radical Chain ◽  
Radical Chain Reaction

Catalytic enantioselective synthesis of tetrahydrofurans, which are found in the structures of many biologically active natural products, via a transition-metal catalyzed-hydrogen atom transfer (TM-HAT) and radical-polar crossover (RPC) mechanism is described herein. Hydroalkoxylation of non-conjugated alkenes proceeded efficiently with excellent enantioselectivity (up to 94% ee) using a suitable chiral cobalt catalyst, <i>N</i>-fluoro-2,4,6-collidinium tetrafluoroborate, and diethylsilane. Surprisingly, absolute configuration of the product was highly dependent on the steric hindrance of the silane. Slow addition of the silane, the dioxygen effect in the solvent, thermal dependency, and DFT calculation results supported the unprecedented scenario of two competing selective mechanisms. For the less-hindered diethylsilane, a high concentration of diffused carbon-centered radicals invoked diastereoenrichment of an alkylcobalt(III) intermediate by a radical chain reaction, which eventually determined the absolute configuration of the product. On the other hand, a more hindered silane resulted in less opportunity for radical chain reaction, instead facilitating enantioselective kinetic resolution during the late-stage nucleophilic displacement of the alkylcobalt(IV) intermediate.

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