ScholarLens Back to search
2010•Biocatalysis and BiotransformationRequires access

Chemoenzymatic synthesis of enantiopure 1-phenyl-2-haloethanols and their esters

Sina M. Lystvet, Bård Helge Hoff, THORLEIF ANTHONSEN, Elisabeth Egholm Jacobsen

Open publisher page 10 citations

Abstract

Several secondary haloalcohols have been resolved by esterification catalyzed by lipases A and B from Candida antarctica (CALA and CALB, respectively). Immobilized CALB (Novozym 435) gave better selectivities and faster reaction rates than CALA (Novozyme 735) with all of the substrates. Vinyl butanoate was the favoured acyl donor compared to vinyl acetate due to remarkably faster reactions. The alcohols (R)-2a, (R)-2c and the butanoates (S)-3a-c have been isolated with 98–99% enantiomeric excess (ee) in good yields.

About this research paper

What this paper is about

Several secondary haloalcohols have been resolved by esterification catalyzed by lipases A and B from Candida antarctica (CALA and CALB, respectively). Immobilized CALB (Novozym 435) gave better selectivities and faster reaction rates than CALA (Novozyme 735) with all of the substrates. Vinyl butanoate was the favoured acyl donor compared to vinyl acetate due to remarkably faster reactions. The alcohols (R)-2a, (R)-2c and the butanoates (S)-3a-c have been isolated with 98–99% enantiomeric excess (ee) in good yields.

Why it matters

OpenAlex reports 10 citations for this work. Citation counts describe recorded attention and do not establish research quality.

Key contribution

A contribution statement is not available in the OpenAlex record.

Method / approach

Method details are not available in the OpenAlex metadata.

Main findings

Findings are not separately available in the OpenAlex metadata.

Limitations

Limitations are not available in the OpenAlex metadata.

Applications

Application details are not available in the OpenAlex metadata.

Available abstract

Several secondary haloalcohols have been resolved by esterification catalyzed by lipases A and B from Candida antarctica (CALA and CALB, respectively). Immobilized CALB (Novozym 435) gave better selectivities and faster reaction rates than CALA (Novozyme 735) with all of the substrates. Vinyl butanoate was the favoured acyl donor compared to vinyl acetate due to remarkably faster reactions. The alcohols (R)-2a, (R)-2c and the butanoates (S)-3a-c have been isolated with 98–99% enantiomeric excess (ee) in good yields.

Key concepts: Candida antarctica, Enantiopure drug, Chemistry, Vinyl acetate, Enantiomer, Organic chemistry, Enantiomeric excess, Catalysis

Related papers

Related paper 1Related paper 2Related paper 3
Back to paper searchBrowse research topicsOriginal source
Chemoenzymatic synthesis of enantiopure 1-phenyl-2-haloethanols and their esters — Research Paper | ScholarLens