Enantioselective Synthesis of α-Hydroxy Ketones via Benzaldehyde Lyase-Catalyzed C−C Bond Formation Reaction

(R)‐Benzoins and (R)‐2‐hydroxypropiophenone derivatives are formed on a preparative scale by benzaldehyde lyase (BAL)‐catalyzed C−C bond formation from aromatic aldehydes and acetaldehyde in aqueous buffer/DMSO solution with remarkable ease in high chemical yield and high optical purity. The substra...

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Published inAdvanced synthesis & catalysis Vol. 344; no. 1; pp. 96 - 103
Main Authors Demir, Ayhan S., Şeşenoglu, Özge, Eren, Elif, Hosrik, Birsu, Pohl, Martina, Janzen, Elena, Kolter, Doris, Feldmann, Ralf, Dünkelmann, Pascal, Müller, Michael
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 01.01.2002
WILEY‐VCH Verlag GmbH
Subjects
benzoin condensation
biocatalyst
carboligation
hydroxy ketones
thiamin diphosphate
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Summary:(R)‐Benzoins and (R)‐2‐hydroxypropiophenone derivatives are formed on a preparative scale by benzaldehyde lyase (BAL)‐catalyzed C−C bond formation from aromatic aldehydes and acetaldehyde in aqueous buffer/DMSO solution with remarkable ease in high chemical yield and high optical purity. The substrate range of this thiamin diphosphate‐dependent enzyme was examined with respect to a broad applicability of this benzoin condensation‐type reaction in stereoselective synthesis.
Bibliography:istex:D7087B8DF654A027D7C57D909DD65D4A5E973D37
ark:/67375/WNG-7P9V4N0T-Q
ArticleID:ADSC96
ISSN:1615-4150
1615-4169
DOI:10.1002/1615-4169(200201)344:1<96::AID-ADSC96>3.0.CO;2-Z