118100-60-0

Upstream product

• 93-91-4 1-phenylbutan-1,3-dione 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 5381-93-1 (4R)-4-hydroxy-4-phenylbutan-2-one 
• 1896-62-4 (E)-benzalacetone 
• 116660-74-3 (-)-(3R)-3-hydroxy-1-phenylbutan-1-one 
• 34501-28-5 (+/-)-(RS)-((2SR,3SR)-3-methyloxiranyl)-phenylmethanol 
• 105735-20-4 (3S)-(+)-3-hydroxy-1-phenylbutan-1-one 

Relevant academic research and scientific papers

Asymmetric chemoenzymatic synthesis of 1,3-diols and 2,4-disubstituted aryloxetanes by using whole cell biocatalysts

Regio- and stereo-selective reduction of substituted 1,3-aryldiketones, investigated in the presence of different whole cell microorganisms, was found to afford β-hydroxyketones or 1,3-diols in very good yields (up to 95%) and enantiomeric excesses (up to 96%). The enantiomerically enriched aldols, obtained with the opposite stereo-preference by baker's yeast and Lactobacillus reuteri DSM 20016 bioreduction, could then be diastereoselectively transformed into optically active syn- or anti-1,3-diols by a careful choice of the chemical reducing agent (diastereomeric ratio up to 98 : 2). The latter, in turn, were stereospecifically cyclized into the corresponding oxetanes in 43-98% yields and in up to 94% ee, thereby giving a diverse selection of stereo-defined 2,4-disubstituted aryloxetanes.

Asymmetric synthesis of new chiral 1,2- and 1,3-diols

Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine-BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4 and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, 1H and 13C NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine-BH 3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.

Exploring the potential of some yeast strains in the stereoselective synthesis of aldol reaction products and its reduced 1,3-dialcohol derivatives

The behavior of two yeast strains has been studied under different conditions. Both microorganims catalyzed the aldol reaction between activated aldehydes and acetone when a large amount of the latter was present in the reaction medium producing, with mod

Catalytic 1,3-difunctionalisation of organic backbones through a highly stereoselective, one-pot, boron conjugate-addition/reduction/oxidation process

A simple one-pot, three-step synthetic route to chiral 1,3-amino alcohols and 1,3-diols has been established. Considering the overall stereocontrol of the synthetic protocol, the first and key step is an enantioselective β-boration of α,β-unsaturated imin

Enzyme directed diastereoselectivity in chemical reductions: Studies towards the preparation of all four isomers of 1-phenyl-1,3-butanediol

Enzymes play an important role in guiding the diastereoselectivity of the final products during the chemical reduction of the intermediates (R)- and (S)-3-hydroxy-1-phenyl-1-butanone, prepared by bioreduction of 1-phenyl-1,3-butadione. For example, the pr

Solvent-dependent diastereoselectivities in reductions of β-hydroxyketones by Sml2

The reductions of a series of β-hydroxyketones by Sml2 were examined in THF, DME, and CH3CN using methanol as a proton source. Reductions in THF and DME typically lead to the syn diastereomer with DME providing higher diastereoselect

Enzymatic Synthesis of Chiral 1-Phenyl-1,2- and 1,3-diols via Chiral Epoxy Alcohols

Chiral epoxy alcohols have been prepared by asymmetric reduction of 1-phenyl-2,3-epoxybutan-1-one with baker's yeast, or by enantioselective esterification of racemic 1-phenyl-2,3-epoxybutan-1-one with lipase PS.The epoxyalcohols obtained were reduced with lithium aluminium hydride to afford chiral 1-phenylbutane-1,2- and 1,3-diols.The absolute configurations of the epoxy alcohols and diols were determined by use of modified Mosher's method or by comparison with the diols, which were prepared from benzoylacetone via chiral enols by use of baker's yeast and lipase PS.

Ruthenium(II)-BINAP Catalysed Stereoselective Homogeneous Hydrogenation of 1,3-Diketones

Ruthenium-BINAP catalysed hydrogenation of 1,3-diketonesa gives 1,3-diols with extremely high diastereo- and anantio-selectivity.