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


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

ADVANCED SYNTHESIS & CATALYSIS, vol.344, no.1, pp.96-103, 2002 (Peer-Reviewed Journal) identifier

  • 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, 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

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.