Continuous Flow Preparation of Enantiomerically Pure BINOL(s) by Acylative Kinetic Resolution

The stereochemistry of epoxide carbonylation using bimetallic [Lewis acid]+[Co(CO)4]- complexes is reported. The achiral complex [(salph)Al(THF)2][Co(CO)4] stereospecifically carbonylates cis- and trans-2-butene oxide to the trans- and cis-β-lactones, respectively. Preliminary experiments regarding the carbonylative kinetic resolution of racemic trans-2-butene oxide using the enantiomerically pure complex [(R,R-salcy)Al(THF)2][Co(CO)4] are also reported.

Download Full-text

Ammonium formate as a green hydrogen source for clean semi-continuous enzymatic dynamic kinetic resolution of (+/−)-α-methylbenzylamine

RSC Advances ◽

10.1039/c4ra00462k ◽

2014 ◽

Vol 4 (26) ◽

pp. 13620-13625 ◽

Cited By ~ 11

Author(s):

Amanda S. de Miranda ◽

Rodrigo O. M. A. de Souza ◽

Leandro S. M. Miranda

Keyword(s):

Continuous Flow ◽

Kinetic Resolution ◽

Ammonium Formate ◽

Flow Conditions ◽

Dynamic Kinetic Resolution

The chemoenzymatic dynamic kinetic resolution of (+/−)-α-methylbenzylamine under continuous flow conditions in the presence of Pd/BaSO4as racemization catalyst and ammonium formate as reductant is described.

Download Full-text

Synthesis of enantiomerically pure alcohols and amines via biocatalytic deracemisation methods

Catalysis Science & Technology ◽

10.1039/c9cy01539f ◽

2019 ◽

Vol 9 (20) ◽

pp. 5487-5503 ◽

Cited By ~ 14

Author(s):

Musa M. Musa ◽

Frank Hollmann ◽

Francesco G. Mutti

Keyword(s):

Kinetic Resolution ◽

Enantiomeric Excess ◽

Enantiomerically Pure ◽

Theoretical Maximum

Deracemisation via chemo-enzymatic or multi-enzymatic approaches is the optimum substitute for kinetic resolution, which suffers from the limitation of a theoretical maximum 50% yield albeit high enantiomeric excess is attainable.

Download Full-text

A Chemoenzymatic Dynamic Kinetic Resolution Approach to Enantiomerically Pure (R)- and (S)-Duloxetine

The Journal of Organic Chemistry ◽

10.1021/jo2003665 ◽

2011 ◽

Vol 76 (10) ◽

pp. 3917-3921 ◽

Cited By ~ 56

Author(s):

Annika Träff ◽

Richard Lihammar ◽

Jan-E. Bäckvall

Keyword(s):

Kinetic Resolution ◽

Dynamic Kinetic Resolution ◽

Enantiomerically Pure

Download Full-text

Immobilized Whole-Cell Transaminase Biocatalysts for Continuous-Flow Kinetic Resolution of Amines

Catalysts ◽

10.3390/catal9050438 ◽

2019 ◽

Vol 9 (5) ◽

pp. 438 ◽

Cited By ~ 14

Author(s):

Zsófia Molnár ◽

Emese Farkas ◽

Ágnes Lakó ◽

Balázs Erdélyi ◽

Wolfgang Kroutil ◽

...

Keyword(s):

Continuous Flow ◽

Kinetic Resolution ◽

Sol Gel ◽

Chiral Amines ◽

Flow Mode ◽

Immobilized Cell ◽

Hollow Silica ◽

E Coli ◽

Sol Gel Process ◽

Racemic Amines

Immobilization of transaminases creates promising biocatalysts for production of chiral amines in batch or continuous-flow mode reactions. E. coli cells containing overexpressed transaminases of various selectivities and hollow silica microspheres as supporting agent were immobilized by an improved sol-gel process to produce immobilized transaminase biocatalysts with suitable stability and mechanical properties for continuous-flow applications. The immobilized cell-based transaminase biocatalyst proved to be durable and easy-to-use in kinetic resolution of four racemic amines 1a–d. The batch and continuous-flow mode kinetic resolutions with transaminase biocatalyst of opposite stereopreference provided access to both enantiomers of the corresponding amines. By using the most suitable immobilized transaminase biocatalysts, this study describes the first transaminase-based approach for the production of both pure enantiomers of 1-(3,4-dimethoxyphenyl)ethan-1-amine 1d.

Download Full-text