187671-47-2Relevant academic research and scientific papers
Enantiopure building blocks for the synthesis of 3-methyl-2-alkanols. Diastereoselective methylmetal addition to a chiral 2-methylaldehyde followed by lipase catalysed esterification
Larsson, Michael,Andersson, Jimmy,Liu, Rong,Hoegberg, Hans-Erik
, p. 2907 - 2915 (2007/10/03)
The racemic synthetic building block (2R*,3R*)-3-methyl-4- (phenylsulfanyl)butan-2-ol (2R*,3R*)-2 was obtained in a high diastereomeric ratio [95:5, (2R*,3R*)/(2R*,3S*)-ratio] by Lewis acid catalysed dimethylzinc addition to racemic 2-methyl-3- (phenylsul
Preparation of Sulfur-Containing Optically Active Secondary Alcohols Based on Pichia farinosa-Catalyzed anti-Prelog-Rule Reduction as the Key Step
Ohtsuka, Yoshikazu,Katoh, Osamu,Sugai, Takeshi,Ohta, Hiromichi
, p. 483 - 491 (2007/10/03)
A Pichia farinosa IAM 4682 mediated reduction of sulfur containing ketones afforded secondary alcohols with (R)-absolute configuration. For example, 4-(phenylthio)-2-butanone and 4-(phenylsulfonyl)-2-butanone afforded (R)-4-(phenylthio)-2-butanol (91%ee) in 90% yield and (R)-4-(phenylsulfonyl)-2-butanol (97%ee) in 94% yield, respectively. In the case that the ee of the product was not satisfactory, any contaminating (S)-enantiomer was selectively oxidized by Rhodococcus rhodochrous IFO 15564 to leave pure (R)-enantiomer. The substrate specificity of Pichia farinosa-mediated reduction and Rhodococcus rhodochrous-mediated oxidation was further examined.
Biotransformation of αβ-unsaturated carbonyl compounds: sulfides, sulfoxides, sulfones, nitriles and esters by yeast species: carbonyl group and carbon-carbon double bond reduction
Koul, Surinder,Crout, David H. G.,Errington, William,Tax, Jiri
, p. 2969 - 2988 (2007/10/03)
The reduction of αβ-unsaturated ketones with γ-sulfide, sulfoxide, sulfone, nitrile and ester functions has been investigated.Both C=O and C=C reduction was observed.In the sulfur series, C=O bond reduction was always observed, but significant C=C bond reduction was observed only with the sulfide.The unsaturated nitriles gave the corresponding alcohols as the major bioreduction product, with smaller but significant amounts of fully reduced product.A similar result was obtained with the ester substrate.Relative and absolute configurations of bioreduction products were determined.A comparison was made between reductions catalysed by bakers' yeast (Saccharomyces cerevisiae) and by other yeasts (Zygosaccharomyces rouxii, Pichia capsulata, P. farinosa, Candida chalmersi and C. diddensiae).The tendency of Z. rouxii to give products enantiomeric with thouse obtained using S. cerevisiae was noted.The relationship between substrate structure and the stereochemistry of C=C double bond reduction is discussed.
