103729-81-3

Upstream product

• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 93-91-4 1-phenylbutan-1,3-dione 
• 98-86-2 acetophenone 
• 97946-11-7 (+/-)-(Z)-1-(dimethylphenylsilyl)-1-phenyl-2-butene 
• 97946-09-3 (+/-)-(E)-1-(dimethylphenylsilyl)-1-phenyl-2-butene 
• 1896-62-4 (E)-benzalacetone 
• 100103-32-0 4-phenyl-4-(dimethylphenylsilyl)butan-2-one 
• 122420-36-4 1-phenyl-3-(phenyldimethylsilyl)-1-butanone 
• 13505-39-0 3-hydroxy-1-phenyl-butan-1-one 
• 406681-12-7 2,2,4-trimethyl-6-phenyl-[1,3]dioxane 
• 100-52-7 benzaldehyde 

Downstream Products

• 118918-39-1 (+)-(4R)-4-acetyloxy-4-phenyl-2-butanone 
• 578020-31-2 (3R)-3-hydroxy-1-phenylbutan-1-one acetate 

Relevant academic research and scientific papers

TiCl4-mediated reduction of 1,3-diketones with BH3-pyridine complex: A highly diastereoselective method for the synthesis of syn-1,3-diols

(formula presented) 1,3-Diketones can be reduced in high yields and with excellent diastereoselectivity to the corresponding syn-1,3-diols by carrying out the reaction with BH3-pyridine complex in CH2Cl2 at -78°C in the pr

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

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

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.

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

Albumin-directed stereoselective reduction of 1,3-diketones and β-hydroxyketones to anti diols

The reduction of 1,3-diketones and β-hydroxyketones with NaBH 4 in aqueous acetonitrile is highly stereoselective in the presence of stoichiometric amounts of bovine or human albumin, giving anti 1,3-diols with d.e. up to 96%. The same reaction, without albumin, gives syn and anti 1,3-diols in approximately 1:1 ratio. The presence of an aromatic carbonyl group is essential for diastereoselectivity in the NaBH4/albumin reduction of both 1,3-diketones and β-hydroxyketones. Thus, 3-hydroxy-1-(p-tolyl)-1- butanone is stereoselectively reduced in the presence of albumin, while reduction of its isomer 4-(p-tolyl)-4-hydroxy-2-butanone is not stereoselective. The albumin-controlled reduction is not stereospecific as both enantiomers of 1-aryl-3-hydroxy-1-butanones are reduced to diols with identical stereoselectivities. Circular dichroism of the bound substrates confirms that aromatic ketones are recognized by the protein's IIA binding site. Binding studies also suggest that 1,3-diketones are recognized in their enol form. From the effect of pH on binding of a diketone it is concluded that, in the complex with the substrate, ionizable residues His242 and Lys199 are in the neutral and protonated forms, respectively. A homology model of BSA was obtained and docking of model substrates confirms the preference of the protein for aromatic ketones. Modelling of the complexes with the substrates also allows us to propose a mechanism for the reduction of 1,3-diketones in which the chemoselective reduction of the first (aliphatic) carbonyl is followed by the diastereoselective reduction of the second (aromatic) carbonyl. The role of albumin is thus a combination of chemo- and stereocontrol.

Sm(II)-mediated reduction in water: Importance of the additive in the proportionation of SmCl3 and Sm

Mechanistic studies of the SmCl3-Sm system in water were carried out. The addition of N,N-dimethylacetoamide (DMA) enhanced the reactivity of the one-electron reduction. According to the ultraviolet-visible (UV-vis) analysis, DMA was found to accelerate proportionation of SmCl3 and Sm.

Reduction of β-hydroxyketones by Sml2/H2O/ Et3N

(Chemical Equation Presented) Reduction of a series of β- hydroxyketones by Sml2/H2O/Et3N provided 1,3-diols in quantitative yields. The reactions were exceedingly clean with no byproduct formation, negating the need for f

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

Diastereomer-differentiating hydrolysis of 1,3-diol-acetonides: A simplified procedure for the separation of syn-and anti-1,3-diols

(formula presented) A new method to facilitate the separation of diastereomeric syn- and anti-1,3-diols is described. The method relies on the different hydrolysis rates of the corresponding diastereomeric acetonides. Treatment of a dichloromethane solution of syn- and anti-1,3-diol-acetonide with a catalytic amount of diluted aqueous hydrochloric acid leads to the selective cleavage of the anti diastereomer. The resulting anti-1,3-diol can be easily separated from the unchanged syn-1,3-diol-acetonide.