Manufacturing Process Development for Belzutifan, Part 5: A Streamlined Fluorination–Dynamic Kinetic Resolution Process

2021 ◽  
Author(s):  
Tao Wang ◽  
Eric M. Phillips ◽  
Stephen M. Dalby ◽  
Eric Sirota ◽  
Stephanus Axnanda ◽  
...  
Keyword(s):  
Manufacturing Process ◽  
Kinetic Resolution ◽  
Process Development ◽  
Dynamic Kinetic Resolution ◽  
Resolution Process

Dynamic Kinetic Resolution of Phosphinic Acid Derivatives via Nucleophilic­ Substitution at Phosphorus Center

Synthesis ◽  
2018 ◽  
Vol 50 (24) ◽  
pp. 4922-4932
Author(s):  
Piotr Borowski ◽  
Marek Stankevič ◽  
Dorota Strzelecka ◽  
Olga Bąk
Keyword(s):  
Organophosphorus Compound ◽  
Kinetic Resolution ◽  
Phosphinic Acid ◽  
Predominant Formation ◽  
Chiral Alcohols ◽  
Chiral Alcohol ◽  
Dynamic Kinetic Resolution ◽  
Resolution Process

Reaction of racemic phosphinic acid derivatives with chiral alcohols proceeds with predominant formation of one diastereomer. The highest level of enrichment has been obtained for transesterfication of racemic methyl benzylphenylphosphinate (64% de). The outcome of the reaction depends on both the structure of chiral alcohol and the starting organophosphorus compound. The results strongly suggest that the nature of the observed phenomena is not a classical equilibration of intermediates found in dynamic kinetic resolution process but is a result of a different reactivity of both enantiomers of racemic substrate towards the same chiral nucleophile.

scholarly journals Diastereoselective Synthesis of b-Branched a-Amino Acids via Bio-catalytic Dynamic Kinetic Resolution

2021 ◽  
Author(s):  
Fuzhuo Li ◽  
Li-Cheng Yang ◽  
Jingyang Zhang ◽  
Jason Chen ◽  
Hans Renata
Keyword(s):  
Amino Acids ◽  
Total Synthesis ◽  
Kinetic Resolution ◽  
Diastereoselective Synthesis ◽  
Mechanistic Studies ◽  
Dynamic Kinetic Resolution ◽  
Resolution Process ◽  
Biocatalytic Reaction

We report a biocatalytic transamination method to prepare a broad range of b-branched a-amino acids that proceeds with high diastereo- and enantioselectivity. Mechanistic studies show that the transformation proceeds through a dynamic kinetic resolution process that is unique to the optimal enzyme. To highlight its utility and practicality, the biocatalytic reaction is applied to the synthesis of several cyclic fragments and in the first total synthesis of jomthonic acid A.

Facile construction of three contiguous stereogenic centers via dynamic kinetic resolution in asymmetric transfer hydrogenation of quinolines

2014 ◽  
Vol 50 (83) ◽  
pp. 12526-12529 ◽  
Author(s):  
Mu-Wang Chen ◽  
Xian-Feng Cai ◽  
Zhang-Pei Chen ◽  
Lei Shi ◽  
Yong-Gui Zhou
Keyword(s):  
Phosphoric Acid ◽  
Kinetic Resolution ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Dynamic Kinetic Resolution ◽  
Resolution Process ◽  
Chiral Phosphoric Acid ◽  
Stereogenic Centers ◽  
Facile Route

An efficient and facile route to chiral tetrahydroquinolines with three contiguous stereogenic centers via a dynamic kinetic resolution process has been successfully developed by using chiral phosphoric acid as catalyst and Hantzsch ester as the hydrogen source with up to 89% ee.

Dynamic Kinetic Resolution Process Employing Haloalkane Dehalogenase

ACS Catalysis ◽  
2011 ◽  
Vol 1 (12) ◽  
pp. 1654-1660 ◽  
Author(s):  
Alja Westerbeek ◽  
Wiktor Szymański ◽  
Ben L. Feringa ◽  
Dick B. Janssen
Keyword(s):  
Kinetic Resolution ◽  
Haloalkane Dehalogenase ◽  
Dynamic Kinetic Resolution ◽  
Resolution Process

scholarly journals Diastereoselective Synthesis of b-Branched a-Amino Acids via Bio-catalytic Dynamic Kinetic Resolution

2021 ◽  
Author(s):  
Fuzhuo Li ◽  
Li-Cheng Yang ◽  
Jingyang Zhang ◽  
Jason Chen ◽  
Hans Renata
Keyword(s):  
Amino Acids ◽  
Total Synthesis ◽  
Kinetic Resolution ◽  
Diastereoselective Synthesis ◽  
Mechanistic Studies ◽  
Dynamic Kinetic Resolution ◽  
Resolution Process ◽  
Biocatalytic Reaction

We report a biocatalytic transamination method to prepare a broad range of b-branched a-amino acids that proceeds with high diastereo- and enantioselectivity. Mechanistic studies show that the transformation proceeds through a dynamic kinetic resolution process that is unique to the optimal enzyme. To highlight its utility and practicality, the biocatalytic reaction is applied to the synthesis of several cyclic fragments and in the first total synthesis of jomthonic acid A.

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