Regio- and stereoselective reduction of trans-4-phenylbut-3-en-2-one using carrot, celeriac, and beetroot enzyme systems in an organic solvent

Asymmetric Bio- and Chemoreduction of 2-Benzylidenecyclopentanone Derivatives

“…Similarly, an α,β-unsaturated ketone trans-4-phenylbut-3-en-2-one was regio-and stereoselectively reduced using carrot, celeriac, and beetroot enzyme systems to the corresponding (S)-allylic alcohol in ee's 72-99%. 27 In our case, the baker's yeast reduction of chlorobenzylidenecyclopentanone 3a gave very low isolated yield (5%) and optical purity (ee = 9%) of the corresponding alcohol 7a even after incubating the reaction mixture at 38 o C for 10 days. On the contrary, the 24-hour-bioreduction with Daucus carota root (substrate/carrot, 1/134 (w/w)) delivered alcohol (S)-7a with >99% ee as determined in the crude product (Figure 2, chromatogram (h)), the amount of which was, however, very low after removal of the biomaterial (Scheme 2).…”

From traditional to greener alternatives: potential of plant resources as a biotransformation tool in organic synthesis

“…In a later study, it was erudite that the bakers' yeast chemoselectively reduces alkene in 63 over ketone to yield 64 99 whereas carrot/celeriac root reduces selectively the ketone over alkene to afford 65 . 100 Although both bakers' yeast as well as carrot/celeriac reductions produces stereoselective products (Fig. 11).…”

Tween-20® Enhanced Bioreduction of Acetophenones Promoted by Daucus carota Root

“…Unusual substrates (e.g. graphene oxide) (3), biphasic systems (4), one-pot multistep reactions (5), and even reactions in organic solvents (6) have been reported when using carrots as catalysts. However, the relatively long reaction time (up to 72 h) combined with a high biocatalyst loading (usually 100 g/L) and a low substrate concentration (1 g/L or less) can hamper approaches to reaction scale-up.…”