Enantioselective synthesis of alpha-hydroxy ketones via benzaldehyde lyase-catalyzed C-C bond formation reaction

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Demir A., Sesenoglu O., Eren E., Hosrik B., Pohl M., Janzen E., ...More

ADVANCED SYNTHESIS & CATALYSIS, vol.344, no.1, pp.96-103, 2002 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 344 Issue: 1
• Publication Date: 2002
• Doi Number: 10.1002/1615-4169(200201)344:1<96::aid-adsc96>3.0.co;2-z
• Journal Name: ADVANCED SYNTHESIS & CATALYSIS
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Page Numbers: pp.96-103
• Keywords: benzoin condensation, biocatalyst, carboligation, hydroxy ketones, thiamin diphosphate, FRUCTOSE-DERIVED DIOXIRANE, FLUORESCENS BIOVAR-I, SILYL ENOL ETHERS, BENZOIN CONDENSATION, KINETIC RESOLUTION, THIAZOLIUM SALT, BAKERS-YEAST, BENZOYLFORMATE DECARBOXYLASE, NUCLEOPHILIC ACYLATION, TRIMETHYLSILYL CYANIDE
• Middle East Technical University Affiliated: Yes

Abstract

(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 case 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.