Enantiospecific reduction of prochiral ketones of aromatic type to optically active alcohols in Nigrospora oryzae culture

✍ Scribed by Bogdan Jarosz; Prof. Dr. Antoni Siewiński

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 501 KB
• Volume: 36
• Category: Article
• ISSN: 0233-111X
• DOI: 10.1002/jobm.3620360407

✦ Synopsis

Abstract

The culture of Nigrospora oryzae reduces twelve prochiral ketones of homo‐ and heteroaromatic type (acetophenone, 3‐ and 4‐methylacetophenone, 4‐nitroacetophenone, propiophenone, 2‐acetylnaphtha‐lene, 2‐acetyltiophene, 2‐ and 4‐acetylpyridine, α,α,α‐trifluoroacetophenone, α‐tetralone, 4‐benzoyl‐pyridine) enantiospecifically to corresponding optically active alcohols. The enantiomer of S configuration is in nine cases predominant, R configuration was found in three alcohols. The degree of chemical reduction determined in GC ranged from 20% to almost 100%, while optical purity was from 5% to 100% ee. It is worth noting that the same culture did not reduce 4‐aminoacetophenone, 2‐acetylpyrrole and 2‐acetylindole.