Enzyme catalyzed hydroxymethylation of aromatic aldehydes with formaldehyde. Synthesis of hydroxyacetophenones and (S)-benzoins

Demir A., Ayhan P., Igdir A., Duygu A.

TETRAHEDRON, vol.60, no.31, pp.6509-6512, 2004 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 60 Issue: 31
  • Publication Date: 2004
  • Doi Number: 10.1016/j.tet.2004.06.015
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.6509-6512
  • Keywords: hydroxymethylation, hydroxy ketones, carboligation, enzyme catalysis, benzoin, SILYL ENOL ETHERS, ENANTIOSELECTIVE SYNTHESIS, BENZOIN CONDENSATION, ASYMMETRIC-SYNTHESIS, BENZALDEHYDE LYASE, CARBONYL-COMPOUNDS, ORGANIC-SYNTHESIS, HYDROXY KETONES, ALDOL REACTION, CLEAVAGE
  • Middle East Technical University Affiliated: Yes

Abstract

Benzaldehyde lyase from the Pseudomonas Fluorescens catalyzed reaction of aromatic aldehydes with formaldehyde providing 2-hydroxy-1-arylethan-1-one in high yields via an acyloin linkage. Kinetic resolution of rac-benzoins with formaldehyde providing (S)-benzoins and 2-hydroxy-1-arylethan-1-one via C-C bond cleavage and a bond formation reaction. (C) 2004 Elsevier Ltd. All rights reserved.