Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (R)-2-phenoxypropanoate

2022 ◽  
Author(s):  
Dmitry Gruzdev ◽  
Sergey Vakarov ◽  
Marina Korolyova ◽  
Ekaterina V. Bartashevich ◽  
Andrey Tumashov ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Active Esters

Diastereoselective acylation of a number of racemic methyl-substituted cyclic alkylamines with active esters of 2-phenoxypropanoic acid was studied in detail. Ester of (R)-2-phenoxypropanoic acid and N-hydroxysuccinimide was found to be...

Parallel kinetic resolution of active esters using designer oxazolidin-2-ones derived from phenylglycine

2008 ◽  
Vol 19 (13) ◽  
pp. 1536-1548 ◽  
Author(s):  
Sameer Chavda ◽  
Elliot Coulbeck ◽  
Marco Dingjan ◽  
Jason Eames ◽  
Anthony Flinn ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Active Esters ◽  
Parallel Kinetic Resolution

Parallel kinetic resolution of racemic oxazolidinones using quasi-enantiomeric active esters

2007 ◽  
Vol 18 (21) ◽  
pp. 2515-2530 ◽  
Author(s):  
Ewan Boyd ◽  
Elliot Coulbeck ◽  
Gregory S. Coumbarides ◽  
Sameer Chavda ◽  
Marco Dingjan ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Active Esters ◽  
Parallel Kinetic Resolution

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.

Sign in / Sign up

Export Citation Format

Share Document