Enantiospecific synthesis of optically pure (S)-(+)-3-hydroxy-1-phenyl-1-butanone by bakers' yeast reduction

Abstract

ROBERT CH~NEVERT and SONIA THIBOUTOT. Can. J. Chem. 64, 1599 (1986). Bakers' yeast reduces 1-phenyl-1,3-butanedione with high chemo-and enantio-selectivity to give (S)-(+)-3-hydroxy-1-phenyl-1-butanone. The enantiomeric purity (>98%) was determined by nrnr analysis using a chiral shift reagent and the absolute configuration was determined by correlation with ethyl (S)-(+)-3-hydroxybutyrate.

Baker's Yeast Reduction of β‐Hydroxy Ketones

“…Chênevert,11 for example, described the extraordinary selectivity of the baker's yeast reduction of 1‐phenylbutane‐1,3‐dione to optically pure ( S )‐3‐hydroxy‐1‐phenylbutan‐1‐one. The reaction was found to be unexpectedly chemoselective, with only the carbonyl group at the 3‐position being affected, in spite of the fact that baker's yeast was known to reduce acetophenone.…”

On‐line monitoring of bioreductions via membrane introduction mass spectrometry

“…The bioreduction of 3 has been extensively studied and different results about the presence or absence of isomer 5 have been reported. Using nuclear magnetic resonance (NMR), 4 is the only isomer detected (Ahmad et al, 2004;Chênevert and Thiboutot, 1986). However, when the reaction is monitored by more sensitive techniques such as GC (Fauve and Veschambre, 1988), both isomers 4 and 5 are detected.…”

Yeast‐Mediated Stereoselective Synthesis

“…The reduction of cyclohexane-1,2-dione 38 ( Figure 21.12) gave racemic transcyclohexane-1,2-diol 39 [179,180]. From the reduction of camphorquinone 40, a 63% yield [96] of exo-2-hydroxy camphor 41 and 3-hydroxy camphor 42 was obtained.…”