Biocatalytically Generated Library of Chiral Building Blocks Containing a Quaternary Stereocenter

A biocatalytic strategy for the preparation of a small library of compounds containing a quaternary chiral center is described. By applying halohydrin dehalogenases, four racemic 2,2-disubstituted epoxides were converted in the presence of four nucleophiles to 14 chiral products in yields of 21-47% with 74 to >99% <i>ee</i>. The obtained set of building blocks, which hold diverse functional groups, can be modified to form many high-value organic molecules for use in medicinal chemistry and other areas.

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Publication Details

Journal
Organic Letters
Published
2024-12-03
DOI
https://doi.org/10.1021/acs.orglett.4c03399
Citations
2
Primary Topic
Enzyme Catalysis and Immobilization
Type
article
Field-Weighted Citation Impact
0.47

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article

Biocatalytically Generated Library of Chiral Building Blocks Containing a Quaternary Stereocenter

Robert Junior Kolman, Emina Mehić, Maja Majerić Elenkov, Irena Dokli
2 citations
Organic Letters
Enzyme Catalysis and Immobilization
0.47
article

Biocatalytically Generated Library of Chiral Building Blocks Containing a Quaternary Stereocenter

Robert Junior Kolman, Emina Mehić, Maja Majerić Elenkov, Irena Dokli
article en
2 citations

Abstract

A biocatalytic strategy for the preparation of a small library of compounds containing a quaternary chiral center is described. By applying halohydrin dehalogenases, four racemic 2,2-disubstituted epoxides were converted in the presence of four nucleophiles to 14 chiral products in yields of 21-47% with 74 to >99% <i>ee</i>. The obtained set of building blocks, which hold diverse functional groups, can be modified to form many high-value organic molecules for use in medicinal chemistry and other areas.

Organic LettersVol. 26(49)
Ruđer Bošković Institute (HR)
European Regional Development Fund
Sustainable cities and communities
Openalex Percentile: Top 34%
Enzyme Catalysis and Immobilization
0.47
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