158200-28-3

Upstream product

• 17071-29-3 ethyl 3-oxo-5-phenylpentanoate 
• 53376-62-8 ethyl 3-hydroxy-5-phenylpentanoate 
• 104-53-0 3-phenyl-propionaldehyde 
• 623-48-3 ethyl iodoacetae 
• 1006696-14-5 ethyl 5-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate 
• 647833-19-0 1-(1H-benzo[d]-[1,2,3]triazol-1-yl)-3-phenylprop-2-yn-1-one 
• 1449791-56-3 (3R)-hydroxy-5-phenyl-4-pentynoic acid ethyl ester 

Downstream Products

• 261917-76-4 ethyl (3S)-3-tert-butyldimethylsilyloxy-5-phenylpentanoate 
• 651738-94-2 (S)-3-Hydroxy-5-phenyl-pentanoic acid methoxy-amide 
• 1316861-28-5 C₁₆H₂₂O₄ 
• 103729-39-1 yashabushidiol B (1,7-diphenylheptane-(3R)-(5R)-diol) 
• 261917-78-6 (S)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpentanal 
• 847057-27-6 (S)-6-hydroxy-2-methyl-8-phenyloct-2-en-4-one 
• 911294-52-5 (S)-5-hydroxy-1,7-diphenylhept-1-yn-3-one 
• 911294-32-1 (S)-6-hydroxy-8-phenyloct-2-yn-4-one 
• 847057-26-5 (S)-3-hydroxy-5-phenyl-pentanoic acid methoxymethylamide 
• 651738-95-3 (E)-6-hydroxy-8-phenyl-2-octen-4-one 

Relevant academic research and scientific papers

Efficient asymmetric synthesis of chiral alcohols using high 2-propanol tolerance alcohol dehydrogenase: Sm ADH2 via an environmentally friendly TBCR system

Alcohol dehydrogenases (ADHs) together with the economical substrate-coupled cofactor regeneration system play a pivotal role in the asymmetric synthesis of chiral alcohols; however, severe challenges concerning the poor tolerance of enzymes to 2-propanol and the adverse effects of the by-product, acetone, limit its applications, causing this strategy to lapse. Herein, a novel ADH gene smadh2 was identified from Stenotrophomonas maltophilia by traditional genome mining technology. The gene was cloned into Escherichia coli cells and then expressed to yield SmADH2. SmADH2 has a broad substrate spectrum and exhibits excellent tolerance and superb activity to 2-propanol even at 10.5 M (80%, v/v) concentration. Moreover, a new thermostatic bubble column reactor (TBCR) system is successfully designed to alleviate the inhibition of the by-product acetone by gas flow and continuously supplement 2-propanol. The organic waste can be simultaneously recovered for the purpose of green synthesis. In the sustainable system, structurally diverse chiral alcohols are synthesised at a high substrate loading (>150 g L-1) without adding external coenzymes. Among these, about 780 g L-1 (6 M) ethyl acetoacetate is completely converted into ethyl (R)-3-hydroxybutyrate in only 2.5 h with 99.9% ee and 7488 g L-1 d-1 space-time yield. Molecular dynamics simulation results shed light on the high catalytic activity toward the substrate. Therefore, the high 2-propanol tolerance SmADH2 with the TBCR system proves to be a potent biocatalytic strategy for the synthesis of chiral alcohols on an industrial scale.

Enantioselective Reduction of Ethyl 3-Oxo-5-phenylpentanoate with Whole-Cell Biocatalysts

The biocatalytic stereoselective synthesis of a sterically demanding sec-alcohol (ethyl 3-hydroxy-5-phenylpentanoate) was investigated by starting from the corresponding prochiral ketone. Screening of a collection of microorganisms led to the identificati

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.

Asymmetric transfer hydrogenation of functionalized acetylenic ketones

A systematic study of the asymmetric transfer hydrogenations of functionalized acetylenic ketones and diketones has been completed, together with a total synthesis of (S,S)-(-)-yashabushidiol B. In several cases, excellent enantioselectivities and yields

Bisoxazolidine-catalyzed enantioselective reformatsky reaction

A readily available chiral bisoxazolidine catalyzes the asymmetric Reformatsky reaction between ethyl iodoacetate and aldehydes. In the presence of 10 mol % of the ligand, dimethylzinc, and air, this method produces ethyl 3-hydroxy-3-(4-aryl)propanoates in high yields and in 75 to 80% ee at room temperature within 1 h. In contrast to aromatic substrates, relatively low ee's are obtained with aliphatic aldehydes.

Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation

Deracemisation of aryl substituted β-hydroxy esters by immobilised whole cells of Candida parapsilosis ATCC 7330 gave >99% ee and up to 75% yield of their corresponding (S)-enantiomers. Mechanistic investigation of the deracemisation reaction carried out using a deuterated substrate, ethyl 3-deutero-3-hydroxy-3-phenyl propanoate revealed that while the (S)-enantiomer remains unreacted the (R)-enantiomer undergoes enantioselective oxidation to its corresponding ketoester, which on complementary enantiospecific reduction gives the (S)-enantiomer in high yield and % ee.

Oxidative Cyclization of β-Hydroxyenones with Palladium(II): A Novel Entry to 2,3-Dihydro-4H-pyran-4-ones

(Equation presented) A palladium(II)-mediated oxidative cyclization was found to be effective for the preparation of structurally diverse 2,3-dihydro-4H-pyran-4-ones from the corresponding β-hydroxyenones. Attractive features of this transformation includ

New and stereoselective synthesis of 1,4-disubstituted buten-4-ols (homoallylic alcohol α-adducts) from the corresponding γ-isomers (3,4-disubstituted buten-4-ols) via an acid-catalyzed allyl-transfer reaction with aldehydes

The γ-adducts of homoallylic alcohols 3, derived from aldehydes via the usual reaction with common allylic metals 1, were converted to the corresponding α-adducts 6 by an acid-catalyzed allyl-transfer reaction. In the allyl-transfer reaction, anti-and syn

2,2',5,5'-tetramethyl-4,4'-bis(diphenylphoshino)-3,3'-bithiophene: A new, very efficient, easily accessible, chiral biheteroaromatic ligand for homogeneous stereoselective catalysis

The four-step straightforward synthesis of enantiopure (+)- and (-)- 2,2',5,5'-tetramethyl-4,4'-bis(diphenylphoshino)-3,3'-bithiophene (tetraMe- BITIOP), anew C2-symmetry chelating ligand for transition metals, is described, starting from 2,5-dimethylthiophene. The complexes of this electron-rich diphosphine with Ru(II) and Rh(I) were used as catalysts in some homogeneous hydrogenation reactions of prostereogenic carbonyl functions of α- and β-ketoesters, of prostereogenic carbon-carbon double bonds of substituted acrylic acids, and of N-acetylenamino acids. The enantiomeric excesses were found to be excellent in all the experiments and comparable with the best results reported in the literature for the same reactions, carried out under similar experimental conditions, with the metal complexes of the most popular chiral diphosphine ligands as catalysts.