182417-58-9

Upstream product

• 17071-29-3 ethyl 3-oxo-5-phenylpentanoate 
• 1198356-01-2 (R)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-phenylpentanoate 
• 55282-95-6 ethyl (2E)-5-phenylpent-2-enoate 
• 88842-13-1 (Z-)-ethyl 5-phenylpent-2-enoate 
• 1006696-14-5 ethyl 5-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate 
• 141-97-9 ethyl acetoacetate 
• 100-39-0 benzyl bromide 
• 53376-62-8 ethyl 3-hydroxy-5-phenylpentanoate 
• 104-53-0 3-phenyl-propionaldehyde 
• 623-48-3 ethyl iodoacetae 

Downstream Products

• 153744-07-1 (R)-3-hydroxy-5-phenylvaleric acid 
• 465545-16-8 (3R)-ethyl 5-phenyl-3-trimethylsilyloxy-pentanoate 
• 116332-80-0 (2R,6R)-2-(tert-butyl)-6-(2'-phenylethyl)-1,3-dioxan-4-one 
• 918148-51-3 t-butyl (R)-5-hydroxy-3-oxo-7-phenylheptanoate 
• 86117-01-3 (4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one 
• 465545-17-9 (R)-5-Phenyl-3-trimethylsilanyloxy-pentanal 

Relevant academic research and scientific papers

Asymmetric synthesis of (6R)-4-hydroxy-6-substituted-δ-lactones

A novel approach for the asymmetric synthesis of (6R)-4-hydroxy-6-substituted-δ-lactones has been achieved using asymmetric reduction of a prochiral ketone in the presence of (S)-(?)-diphenyl-prolinol/borane as a key step. The enantiomeric purity of the products was determined by chiral GC.

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.

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.

Asymmetric β-boration of α,β-unsaturated carbonyl compounds promoted by chiral rhodium-bisoxazolinylphenyl catalysts

Chiral rhodium-bisoxazolinylphenyl acetate complexes exhibited high catalytic activity for the β-boration of α,β-unsaturated carbonyl compounds with bis(pinacolato)diboron in the presence of sodium t-butoxide with enantioselectivity up to 97%.

Catalytic asymmetric boration of acyclic α,β-unsaturated esters and nitriles

(Chemical Equation Presented) Asymmetrie β-boration of acyclic α,β-unsaturated carbonyl compounds provides ready access to enantioenriched functionalized organoboron compounds. A range of acyclic unsaturated esters and nitriles reacted with high enantioselectivity and good yields at room temperature using a copper catalyst and planar chiral diphosphine ligands (L).

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.

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.

Diastereoselective synthesis of polypropionates: Cationic couplings of 4-acetoxy-1,3-dioxanes with crotyl-metal reagents

Lewis acids promote the coupling of 4-acetoxy-1,3-dioxanes 1 with crotyl-metal species to generate propionate motifs such as 2. The reactions show a marked dependence on Lewis acid, the crotyl metal species, and the presence and stereochemical disposition of a C5 methyl group. A 1,3-syn methyl relationship is favored in these additions.

A chiral oxazaborolidinone-promoted aldol reaction with a silyl ketene acetal from ethyl 1,3-dithiolane-2-carboxylate. Synthesis of acetate aldols in high enantiomeric purity

Asymmetric synthesis of dithiolane aldols 3 was achieved in good yields by using silyl ketene acetal 1, derived from ethyl 1,3-dithiolate-2-carboxylate, in the chiral oxazaborolidinone (L-1 and D-2)-promoted aldol reaction and desulfurization of 3 resulted in production of acetate aldols 4 in high enantiomeric purity.