Benzaldehyde Lyase-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds

Ayhan P., DEMİR A. G.

ADVANCED SYNTHESIS & CATALYSIS, vol.353, no.4, pp.624-629, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 353 Issue: 4
  • Publication Date: 2011
  • Doi Number: 10.1002/adsc.201000735
  • Journal Name: ADVANCED SYNTHESIS & CATALYSIS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.624-629
  • Keywords: amidation reaction, enzyme catalysis, hydroxamic acids, thiamine diphosphate-dependent enzyme, ALPHA-KETOGLUTARATE DEHYDROGENASE, HYDROXAMIC ACID PRODUCTION, N-ARYLHYDROXAMIC ACIDS, AROMATIC-COMPOUNDS, ARYL, REDUCTION, OXIDATION
  • Middle East Technical University Affiliated: Yes

Abstract

Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with nitroso compounds and furnishes N-arylhydroxamic acids in high yields. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to their reaction with nitroso compounds. The kinetic resolution of rac-2-hydroxy-1,2-diphenylethanones furnished (S)-benzoins and arylhydroxamic acids with high enantioselectivities and conversions.