Enzymatic Desymmetrisation of Prochiral Phosphines and Phosphine <i>P-</i>Sulfides as a Route to <i>P</i>-Chiral Catalysts

The enzyme-catalyzed monoacetylation of prochiral bis (2-hydroxymethylphenyl)methylphosphine and bis (2-hydroxymethylphenyl)phenylphosphine and their <i>P</i>-sulfides gave, in one single step, as a result of desymmetrisation, the corresponding monoacetates in moderate yields and with an...

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Bibliographic Details
Main Authors: Lidia Madalińska, Piotr Kiełbasiński, Małgorzata Kwiatkowska
Format: Article
Language:English
Published: MDPI AG 2022-01-01
Series:Catalysts
Subjects:
Online Access:https://www.mdpi.com/2073-4344/12/2/171
Description
Summary:The enzyme-catalyzed monoacetylation of prochiral bis (2-hydroxymethylphenyl)methylphosphine and bis (2-hydroxymethylphenyl)phenylphosphine and their <i>P</i>-sulfides gave, in one single step, as a result of desymmetrisation, the corresponding monoacetates in moderate yields and with an enantiomeric excess of 16 to 98%, depending on the substrate structure and enzyme applied. The absolute configurations of the selected products were determined by a chemical correlation. This led to the conclusion that, in the case of phosphines, phosphine oxides and phosphine sulfides enzymes preferentially produce compounds of the same spatial arrangement. The new compounds obtained will be transformed into chiral catalysts/ligands.
ISSN:2073-4344