111044-00-9

Upstream product

• 67-56-1 methanol 
• 111636-13-6 4-hydroxy-4-phenyl-butyric acid ethyl ester 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 71-43-2 benzene 
• 2051-95-8 succinylbenzene 
• 100-52-7 benzaldehyde 

Downstream Products

• 406218-17-5 (R)-4-hydroxy-4-phenylbutyramide 
• 111138-03-5 (R)-4-phenylbutyrolactone 
• 1376191-46-6 (2S)-N-allyl-2-phenylpyrrolidine 
• 1376191-20-6 C₂₇H₃₅N 
• 1006-64-0 (S)-2-phenylpyrrolidine 
• 4850-50-4 (R)-(+)-1-Phenylbutane-1,4-diol 
• 164850-19-5 (S)-2-phenyltetrahydrothiophene 
• 1438891-80-5 (2S)-phenyltetrahydrothiophene-1,1-dioxide 

Relevant academic research and scientific papers

Asymmetric Catalytic Reduction of Ketones with Hypervalent Trialkoxysilanes

The catalytic asymmetric reduction of different ketones1 with transient hypervalent silicon hydrides is described. Trialkoxysilanes, upon activation by a small amount of a chiral nucleophile, underwent addition to the carbonyl group, forming th

Biocatalytic Asymmetric Reduction of γ-Keto Esters to Access Optically Active γ-Aryl-γ-butyrolactones

An efficient stereoselective syntheses of a series of functionalized optically active γ-aryl-γ-butyrolactones is achieved by enzymatic asymmetric reduction of the corresponding sterically demanding γ-keto esters employing wild-type and recombinant alcohol dehydrogenases. The best stereoselectivities for the reduction via hydrogen transfer was obtained with two short chain dehydrogenases (SDRs) of complementary stereospecificity from Aromatoleum aromaticum, namely the Prelog-specific NADH-dependent (S)-1-phenylethanol dehydrogenase [(S)-PED] and the anti-Prelog-specific (R)-1-(4-hydroxyphenyl)-ethanol dehydrogenase [(R)-HPED], respectively.Biotransformations catalyzed by both enzymes, followed by TFA-catalyzed cyclization of the resulting γ-hydroxy esters, furnished the respective (S)- and (R)-configured products with exquisite optical purity (up to >99% ee). The synthetic value was demonstrated on preparative scale for the asymmetric bioreduction of the model compound, methyl 4-oxo-4-phenylbutanoate, affording optically pure (S)-γ-phenyl-γ-butyrolactone (>99% ee) in 67–74% isolated yield at 89–95% conversion depending on the applied scale. (Figure presented.).

Methods for the synthesis of chiral sulfur heterocycles and their application in the asymmetric Baylis-Hillman reactions

Enantiomerically pure (2S,6S)-2,6-diphenyltetrahydro-2H-thiopyran, (2S)-2-phenyltetrahydro thiophene, and (2S)-2-phenyltetrahydro-2H-thiopyran were prepared in 70-72% yields and with 86-99% ee via cyclization of the corresponding dimesylate in an SN2 cyclization reaction using sodium sulfide nonahydrate. The results on the application of various chiral sulfides in asymmetric Baylis-Hillman reactions are also described.

Highly enantioselective synthesis of chiral allenes by sequential creation of stereogenic center and chirality transfer in a single pot operation

Chiral allenes are readily accessed in a single pot operation in the reaction of terminal alkynes, aldehydes, chiral secondary amines, and zinc halides in good yields (up to 77% yield) and excellent enantioselectivities (up to 99% ee) in toluene at 120 °C. The reaction proceeds through initial formation of chiral propargylamine intermediates with creation of a new stereogenic center and subsequent chirality transfer via an intramolecular hydride shift to produce chiral allenes with high enantiomeric purities.

Enantioselective hydrosilylation of prochiral ketones catalyzed by chiral BINAP-copper(I) complexes

The CuCl/NaOt-Bu/BINAP system was found to efficiently catalyze the hydrosilylation of aryl alkyl ketones with excellent enantioselectivities by using phenyl methyl silane as a stoichiometric hydride source. High enantiomeric excesses (up to 97%) and excellent yields (up to 99%) were obtained.

Enantioselective, ketoreductase-based entry into pharmaceutical building blocks: Ethanol as tunable nicotinamide reductant

(Chemical Equation Presented) The use of NADH- and NADPH-dependent ketoreductases to access enantioenriched pharmaceutical building blocks is reported. Seven structurally diverse synthons are obtained, including those for atomoxetine (KRED 132), talampanel (RSt-ADH and CPADH), Dolastatin (KRED 132), and fluoxetine (KRED 108/132). Ethanol may be used as stoichiometric reductant, regenerating both nicotinamide cofactors, particularly under four-electron redox conditions. Its favorable thermodynamic and economic profile, coupled with its advantageous dual cosolvent role, suggests a new application for biomass-derived ethanol.

Applications of asymmetric hydrosilylations mediated by catalytic (DTBM-SEGPHOS)CuH

Several aryl ketone precursors useful in the synthesis of known physiologically active compounds have been reduced to the corresponding nonracemic alcohols. The previously reported combination of a catalytic quantity of (R)-(-)-DTBM-SEGPHOS-ligated CuH an

New efficient organic activators for highly enantioselective reduction of aromatic ketones by trichlorosilane

Aryl ketones were reduced to the corresponding alcohols with excellent enantioselectivity (up to 99.7% ee) by Cl3SiH in the presence of a catalytic amount of N-formyl-α′-(2,4,6-triethylphenyl)-L-proline as an activator. Both carboxyl group at the α-position of the activator and 2,4,6-triethylphenyl group at the α′-position were critical for the high enantioselectivity.

Methods of using norfluoxetine

The invention encompasses methods of using racemic and enantiomerically pure norfluoxetine, as well as pharmaceutical compositions, pharmaceutical unit dosage forms, and kits comprising racemic and enantiomerically pure norfluoxetine. In particular, the i

A practical asymmetric synthesis of (R)-fluoxetine and its major metabolite (R)-norfluoxetine

A convenient and chromatography-free synthesis for the enantiomers of fluoxetine and norfluoxetine is described. The synthesis relied on the use of the CBS reduction, and Hofman rearrangement to establish the key common intermediate 5, and enrichment of optical purity of the final product by crystallization as the tartrate salt.