Baker's yeast mediated biohydrogenation of unsaturated compounds containing a methylene group: enantioselective preparation of 2-methyl alkanols from 2-substituted acrolein acetals

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

“…Perhaps the most widely exploited and commercially significant yeasts are the related species and strains of S. cerevisiae , which have been particularly shown to catalyse compounds with carbonyl groups or carbon–carbon bonds. Therefore, they are extensively employed in a variety of formation and dissociation reactions, such as biodehydrogenation, hydrolysis, oxidation and reduction in organic synthesis24, 37, 38, 94.…”

Transformation of Esters into 2‐Substituted Allyl Halides via Tertiary Cyclopropanols: Application in the Stereoselective Synthesis of (2S,3S,7S)‐3,7‐Dimethyl‐2‐pentadecyl Acetate, the Sex Pheromone of the Pine Sawfly Neodiprion sertifer

“…To synthesize the chiral building block 3 we used baker’s yeast mediated biohydrogenation of the methylene‐substituted acetal 14 as the key step 18. The latter was readily obtained from ethyl (benzyloxy)acetate ( 12 )19 by reaction with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide20 to form cyclopropanol 7 .…”

“…(2 S )‐3‐Benzyloxy‐2‐methylpropan‐1‐ol (3): A known method for baker’s yeast mediated reduction18 was modified and adapted for the preparative‐scale synthesis of compound 3 . A solution of acetal 14 (12.00 g, 48.0 mmol) in ethanol (60 mL) was added portionwise (in six portions over a period of 3 d) with stirring and at an internal temperature 34–38 °C to a suspension of pressed baker’s yeast (1200 g) in a buffer solution (pH 5.25) of citric acid monohydrate (26.88 g, 128 mmol) and K 2 CO 3 (15.46 g, 112 mmol) in water (2.4 L).…”

On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering

“…The BY reduction of benzylacrylaldehyde 7 had been already described in the literature [25] to afford modest yields (20%) of nearly enantiomerically pure (R)-2 (ee = 98%) through a slow addition (96 h) of an ethanolic solution of the substrate to the reaction medium.…”

“…[25]. Aldehydes 11, and 12 were prepared according to the following path: the suitable Baylis-Hillman adduct obtained by reaction of the aromatic aldehyde with methyl acrylate in the presence of DABCO (according to procedure 4.2.1) was submitted to HBr rearrangement.…”