116660-74-3

Upstream product

• 175650-77-8 (R)-1-(2-Phenyl-[1,3]dioxolan-2-yl)-propan-2-ol 
• 108-05-4 vinyl acetate 
• 13505-39-0 3-hydroxy-1-phenyl-butan-1-one 
• 1144528-41-5 (R)-1-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butan-1-one 
• 495-41-0 1-phenylbut-2-en-1-one 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 93-89-0 benzoic acid ethyl ester 
• 175650-76-7 (S)-1-(2-Phenyl-[1,3]dioxolan-2-yl)-3-((R)-toluene-4-sulfinyl)-propan-2-ol 
• 175650-75-6 1-(2-Phenyl-[1,3]dioxolan-2-yl)-3-((R)-toluene-4-sulfinyl)-propan-2-one 
• 27773-03-1 ethyl 3,3-(ethylenedioxy)-3-phenylpropanoate 
• 167780-47-4 (R)-2-<1-(2-hydroxypropyl)>-2-phenyl-1,3-dithiane 
• 93-91-4 1-phenylbutan-1,3-dione 

Downstream Products

• 578020-35-6 (2S,4R)-2-phenylpentane-2,4-diol 
• 112420-27-6 anti-(1S,3R)-1-phenylbutane-1,3-diol 
• 118100-60-0 syn-(1R,3R)-1-phenylbutane-1,3-diol 
• 1286722-86-8 C₂₀H₁₉F₃O₄ 

Relevant academic research and scientific papers

Chiral Bipyridine Ligand with Flexible Molecular Recognition Site: Development and Application to Copper-Catalyzed Asymmetric Borylation of α,β-Unsaturated Ketones

A novel chiral bipyridine ligand bearing a flexible side chain with a molecular recognition site enables precise stereocontrol through the cooperative action of metal center and hydrogen bonds. This new chiral ligand was applied to the copper-catalyzed as

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.

Regio- and enantioselective reduction of diketones: Preparation of enantiomerically pure hydroxy ketones catalysed by Candida parapsilosis ATCC 7330

Enantiomerically enriched hydroxy ketones were prepared by the reduction of the corresponding diketones with excellent enantiomeric excess (98%) and in good yields (up to 75%) using whole cells of Candida parapsilosis ATCC 7330. Cyclic diketones, such as 1,2-cyclohexanedione and 1,4-cyclohexanedione, resulted in hydroxy ketones as products. Cyclohexane-1,3-dione and 5,5-dimethylcyclohexane-1,3-dione gave dimerised products, such as 2,2′-(ethane-1,1-diyl)bis(3-hydroxycyclohex-2-enone) and 2,2′-(ethane-1,1-diyl)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) with acetaldehyde generated in situ from whole cells of Candida parapsilosis ATCC 7330, which is reported here for the first time.

A Cu(II)-based strategy for catalytic enantioselective β-borylation of α,β-unsaturated acceptors

Cu(I)-based chemistry has flourished over the last decade because of the reliable use of species such as soft acids. However, the unique nature of Cu(ii) catalysts allows the well-documented Cu(I)-based chemistry to be extended. Prominent advantages of th

Synthesis of new chiral keto alcohols by baker's yeast

Fourteen chiral α- and β-keto alcohols 2a-2r were synthesized by the asymmetric reduction of their corresponding diketones 1a-1r via baker's yeast. In addition, ten corresponding racemic α-keto alcohols were synthesized by the benzoin condensation of their corresponding aldehydes, which were used for the determination of the ee values through their chiral resolution on chiral HPLC. Amongst the 15 diketones, 1j and chiral α-keto alcohols 2i, 2j and chiral β-keto alcohol 2r are novel compounds. Six keto alcohols 2b, 2c, 2d, 2f, 2h and 2p were synthesized by baker's yeast for the first time. There are some studies in the literature where baker's yeast was applied to the diketones 1a, 1g, 1e, 1k and 1n under various conditions different to those reported herein. The yields and the ee values of these studies were not as high as ours. All of the keto alcohols synthesized were characterized by IR, NMR (1H and 13C), and MS. The relationship between the structure of the diketone and the yield, diastereoselectivity and enantiomeric excess is also discussed.

Heterogeneous versus homogeneous copper(II) catalysis in enantioselective conjugate-addition reactions of boron in water

We have developed CuII-catalyzed enantioselective conjugate-addition reactions of boron to α,β-unsaturated carbonyl compounds and α,β,γ,δ-unsaturated carbonyl compounds in water. In contrast to the previously reported CuI catalysis that required organic solvents, chiral CuII catalysis was found to proceed efficiently in water. Three catalyst systems have been exploited: cat. 1: Cu(OH)2 with chiral ligand L1; cat. 2: Cu(OH)2 and acetic acid with ligand L1; and cat. 3: Cu(OAc)2 with ligand L1. Whereas cat. 1 is a heterogeneous system, cat. 2 and cat. 3 are homogeneous systems. We tested 27 α,β-unsaturated carbonyl compounds and an α,β-unsaturated nitrile compound, including acyclic and cyclic α,β-unsaturated ketones, acyclic and cyclic β,β- disubstituted enones, acyclic and cyclic α,β-unsaturated esters (including their β,β-disubstituted forms), and acyclic α,β-unsaturated amides (including their β,β-disubstituted forms). We found that cat. 2 and cat. 3 showed high yields and enantioselectivities for almost all substrates. Notably, no catalysts that can tolerate all of these substrates with high yields and high enantioselectivities have been reported for the conjugate addition of boron. Heterogeneous cat. 1 also gave high yields and enantioselectivities with some substrates and also gave the highest TOF (43 200 h-1) for an asymmetric conjugate-addition reaction of boron. In addition, the catalyst systems were also applicable to the conjugate addition of boron to α,β,γ, δ-unsaturated carbonyl compounds, although such reactions have previously been very limited in the literature, even in organic solvents. 1,4-Addition products were obtained in high yields and enantioselectivities in the reactions of acyclic α,β,γ,δ-unsaturated carbonyl compounds with diboron 2 by using cat. 1, cat. 2, or cat. 3. On the other hand, in the reactions of cyclic α,β,γ,δ-unsaturated carbonyl compounds with compound 2, whereas 1,4-addition products were exclusively obtained by using cat. 2 or cat. 3, 1,6-addition products were exclusively produced by using cat. 1. Similar unique reactivities and selectivities were also shown in the reactions of cyclic trienones. Finally, the reaction mechanisms of these unique conjugate-addition reactions in water were investigated and we propose stereochemical models that are supported by X-ray crystallography and MS (ESI) analysis. Although the role of water has not been completely revealed, water is expected to be effective in the activation of a borylcopper(II) intermediate and a protonation event subsequent to the nucleophilic addition step, thereby leading to overwhelmingly high catalytic turnover. Copyright

Synthesis and Suzuki-Miyaura cross-coupling of enantioenriched secondary potassium β-trifluoroboratoamides: Catalytic, asymmetric conjugate addition of bisboronic acid and tetrakis(dimethylamino)diboron to α,β- unsaturated carbonyl compounds

Enantioenriched potassium β-trifluoroboratoamides have been synthesized via an asymmetric, copper-catalyzed 1,4-addition of tetrahydroxydiboron (BBA) and tetrakis(dimethylamino)-diboron to α,β-Unsaturated amides. These dibora reagents provide access to the desired organotri-fluoroborates using effective and atom economical sources of boron. The copper-catalyzed β-boration is extended to α,β- Unsaturated ketones and esters. The desired potassium organotrifluoroborates are synthesized with yields up to 92% and enantiomeric ratios up to 98:2. The enantioenriched potassium btrifluoroboratoamides are successfully cross-coupled with an array of aryl and heteroaryl chlorides in high yield with complete stereochemical fidelity as the transmetalation proceeds through an SE2 mechanism via an open transition state.

Asymmetric β-boration of α,β-unsaturated carbonyl compounds with chiral Rh[bis(oxazolinyl)phenyl] catalysts

Chiral rhodium[bis(oxazolinyl)phenyl] complexes exhibited high catalytic activity for the β-boration of α,β-unsaturated esters, ketones, and amides with bis(pinacolato)diboron in the presence of sodium tert-butoxide to attain high enantioselectivity of up to 97%. The substrate scope and catalytic mechanism were discussed.

Chiral copper(II)-catalyzed enantioselective boron conjugate additions to α,β-unsaturated carbonyl compounds in water

Copper pins on the boron: The enantioselective 1,4-addition of diboron to α,β-unsaturated compounds proceeds smoothly in the presence of catalytic amounts of Cu(OH)2 and chiral 2,2′-bipyridine ligand in water. A wide substrate scope of α,β-unsaturated carbonyl compounds, including acyclic, cyclic, and β,β-disubstituted enones, α,β-unsaturated esters, amides, and a nitrile, has been shown. Copyright

Metal-free catalytic boration at the β-position of α,β-unsaturated compounds: A challenging asymmetric induction

Enantiomerlcally enriched secondary organoboronates containing β-carbonyl functional groups have been prepared using an unprecedented organocatalytic system (see scheme). The use of chiral tertiary phosphorus compounds induced ee values of up to 95 % in the absence of transition metals. (Figure Presented).