Chemoenzymatic dynamic kinetic resolution as a key step in the enantioselective synthesis of (S)-salbutamol

2011 ◽  
Vol 76 (7) ◽  
pp. 919-927 ◽  
Author(s):  
Annika Träff ◽  
Carmen E. Solarte ◽  
Jan-E. Bäckvall
Keyword(s):  
Burkholderia Cepacia ◽  
Kinetic Resolution ◽  
Enantiomeric Excess ◽  
Enantioselective Synthesis ◽  
Dynamic Kinetic Resolution

The synthesis of (S)-salbutamol is described. By utilizing DKR in the enantiodetermining step, employing Burkholderia cepacia lipase (PS-IM), (S)-acetate ((S)-6) was obtained in excellent enantiomeric excess (98%). The subsequent transformations yielded the salt of (S)-salbutamol with retained stereochemistry.

scholarly journals Lipase Immobilized on MCFs as Biocatalysts for Kinetic and Dynamic Kinetic Resolution of sec-Alcohols

Catalysts ◽  
2021 ◽  
Vol 11 (4) ◽  
pp. 518
Author(s):  
Dominika Stradomska ◽  
Monika Heba ◽  
Aleksandra Czernek ◽  
Nikodem Kuźnik ◽  
Danuta Gillner ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Enantiomeric Excess ◽  
Enantioselective Synthesis ◽  
Transesterification Reaction ◽  
Methyl Groups ◽  
Dynamic Kinetic Resolution ◽  
Cyclopentadienyl Ligands ◽  
Cellular Foams ◽  
Ru Complexes ◽  
Isopropenyl Acetate

Dynamic kinetic resolution (DKR) is one of the most attractive methods for enantioselective synthesis. In the reported studies, lipase B from Candida antarctica (CALB) immobilized on siliceous mesoporous cellular foams (MCF) functionalized with different hydrophobic groups, and two ruthenium complexes with substituted cyclopentadienyl ligands were investigated as catalysts for the chemoenzymatic DKR of (rac)-1-phenylethanol, using Novozym 435 as a benchmark biocatalyst. Studies on the (rac)-1-phenylethanol transesterification reaction showed that CALB supported on MCFs grafted with methyl groups is a promising biocatalyst and isopropenyl acetate is a preferable acylation agent. Both Ru-complexes activated by K3PO4 or t-BuOK, proved to be effective catalysts of the racemization reaction. The final DKR experiments using all catalysts combinations singled out, gave 96% conversion, and (R)-1-phenylethyl acetate enantiomeric excess of 98% in 8 h using K3PO4 activator.

Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones

2017 ◽  
Vol 129 (9) ◽  
pp. 2494-2498 ◽  
Author(s):  
Sri Krishna Nimmagadda ◽  
Sharath Chandra Mallojjala ◽  
Lukasz Woztas ◽  
Steven E. Wheeler ◽  
Jon C. Antilla
Keyword(s):  
Kinetic Resolution ◽  
Enantioselective Synthesis ◽  
Dynamic Kinetic Resolution

Dynamic Kinetic Resolution and Desymmetrization of Enantiotopic Groups by Cyclodehydration of Racemic or Prochiralδ-Oxoesters with (R)-Phenylglycinol: Enantioselective Synthesis of Piperidines

2002 ◽  
Vol 114 (2) ◽  
pp. 345-348 ◽  
Author(s):  
Mercedes Amat ◽  
Margalida Cantó ◽  
Núria Llor ◽  
Viviana Ponzo ◽  
Maria Pérez ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Enantioselective Synthesis ◽  
Dynamic Kinetic Resolution

Enantioselective Synthesis of (R)-Bufuralol via Dynamic Kinetic Resolution in the Key Step

2010 ◽  
Vol 75 (13) ◽  
pp. 4596-4599 ◽  
Author(s):  
Eric V. Johnston ◽  
Krisztián Bogár ◽  
Jan-E. Bäckvall
Keyword(s):  
Kinetic Resolution ◽  
Enantioselective Synthesis ◽  
Dynamic Kinetic Resolution

Dynamic Kinetic Resolution and Desymmetrization Processes: A Straightforward Methodology for the Enantioselective Synthesis of Piperidines.

ChemInform ◽  
2007 ◽  
Vol 38 (6) ◽  
Author(s):  
Mercedes Amat ◽  
Oriol Bassas ◽  
Nuria Llor ◽  
Margalida Canto ◽  
Maria Perez ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Enantioselective Synthesis ◽  
Dynamic Kinetic Resolution
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