4564-82-3

Upstream product

• 1528-39-8 3-phenyl-2-pentanone 
• 2439-43-2 (2RS)-2-phenylbutanal 
• 74-88-4 methyl iodide 
• 872045-33-5 (1-methoxybut-1-en-2-yl)benzene 
• 75-16-1 methylmagnesium bromide 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 4165-86-0 (E)-(1-ethylpropenyl)benzene 
• 4165-78-0 (Z)-(1-ethylpropenyl)benzene 
• 103-79-7 1-phenyl-acetone 
• 93-55-0 1-phenyl-propan-1-one 
• 917-64-6 methyl magnesium iodide 
• 18006-13-8 methyltriisopropoxytitanium(IV) 
• 96-22-0 pentan-3-one 
• 87437-00-1 3-diphenoxyphosphoryloxypent-2-ene 

Downstream Products

• 1095419-50-3 3-phenylpent-2-ene 
• 138841-73-3 4-Ethyl-3-methyl-2-phenyl-2H-isoquinolin-1-one 
• 138841-75-5 4-Ethyl-3-methyl-2-p-tolyl-2H-isoquinolin-1-one 
• 138841-74-4 4-Ethyl-3-methyl-2-o-tolyl-2H-isoquinolin-1-one 

Relevant academic research and scientific papers

Enantioselective Hydroazidation of Trisubstituted Non-Activated Alkenes

A one-pot procedure for the enantioselective hydroazidation of non-activated trisubstituted alkenes is described. Hydroboration with monoisopinocampheylborane (IpcBH2) provides dialkylboranes that are in situ selectively converted into monoalkyl-substituted catecholboranes; these undergo radical azidation upon treatment with benzenesulfonyl azide and a radical initiator. Enantiomerically enriched azides were thus obtained in yields of 59–81 % and enantioselectivities of up to 94:6 e.r. (98:2 e.r. if the intermediate dialkylborane is purified by crystallization). A rapid access to enantiomerically pure (+)-rodocaine is also described. The use of other arenesulfonyl radical traps enables enantioselective hydroallylation, hydrosulfanylation, and hydrobromination reactions with yields of 71–86 %.

Dynamic Reductive Kinetic Resolution of Benzyl Ketones using Alcohol Dehydrogenases and Anion Exchange Resins

Dynamic reductive kinetic resolutions of racemic 3-arylalkanones have been performed by the proper combination of an alcohol dehydrogenase and a basic anionic resin. The best results were found for the bioreduction with the alcohol dehydrogenase type A from Rhodococcus ruber DSM 44541 overexpressed in Escherichia coli (E. coli/ADH-A) and the commercially available evo-1.1.200, while the Amberlite IRA-440 C and the DOWEX-MWA-1 resins allowed efficient in situ racemizations. Reaction conditions were optimized in terms of enzyme source and loading, type and amount of resin, pH, temperature and reaction times, obtaining a series of (R,R)-substituted propan-2-ols with good conversions and both diastereoselectivity and stereoselectivity. As a proof of concept, the subsequent intramolecular cyclization of a selected propan-2-ol substrate afforded a valuable isochroman heterocycle without any loss of the optical purity.

Dynamic kinetic asymmetric amination of alcohols: From a mixture of four isomers to diastereo- and enantiopure α-branched amines

The first dynamic kinetic asymmetric amination of alcohols via borrowing hydrogen methodology is presented. Under the cooperative catalysis by an iridium complex and a chiral phosphoric acid, α-branched alcohols that exist as a mixture of four isomers undergo racemization by two orthogonal mechanisms and are converted to diastereo- and enantiopure amines bearing adjacent stereocenters. The preparation of diastereo- and enantiopure 1,2-amino alcohols is also realized using this catalytic system.

Studies on the Regioselectivities in the Oxidation of Simple Alkyl Aromatic Hydrocarbons by Molecular Oxygen

The products of the autoxidation of various simple alkyl aromatic hydrocarbons were reduced by LiAlH4, and the alcohols formed were determined by gas chromatography.In the cases of 2-phenylbutane, 3-phenylpentane, and 2-p-tolylbutane a considerable fragmentation of the intermediate tertiary alkoxy radicals was proved.On the basis of the analytical results relative reaction rates of the various C-H bonds in the hydrocarbons studied were calculated.It is shown that the attack at C-H bonds which are not activated by the aromatic nucleus cannot be neglected and may be of great importance for the kinetics of the oxidation of alkyl aromatic hydrocarbons.

Stereoselective Addition of Organotitanium Reagents to Carbonyl Compounds

Titanation of alkyllithium or -magnesium compounds using ClTi(OR)3 results in reagents which show markedly increased diastereofacial selectivity (80 - 90percent) in reactions with α-chiral aldehydes or ketones.Titanation is also the method of choice in Grignard-type additions to substituted cyclohexanones; CH3Ti(OCHMe2)3 (6a) adds predominantly from the equatorial direction, while allyltitanium reagents 11b and 12 show axial preference.Crotyltitanium compounds react with carbonyl compounds to afford primarily adducts having anti-configuration, a process which is of particular value in case of ketones (anti/syn ratios up to 99:1).Titanation of (trimethylsilyl)allyllithium (48) with Ti(OCHMe2)4 reverses regioselectivity in reactions with aldehydes and ketones, β-hydroxy silanes 50 being the only observed products.These have anti-configuration and can be converted either into Z- or E-dienes using the Peterson elimination under basic or acidic conditions, respectively.

Hydroboartion. 62. Monoisopinocampheylborane, an Excellent Chiral Hydroborating Agent for Trans-Disubstituted and Trisubstituted Alkenes. Evidenece for a Strong Steric Dependence in Such Asymmetric Hydroborations

Monoisopinocampheylborane (IpcBH2), the first monoalkylborane chiral hydroborating agent, is capable of reacting with olefins of varying stuctural and steric requiments to produce, in most cases, clean dialkylboranes.IpcBH2 achieves the asymmetric hydroboration of trans-disubstituted and trisubstituted olefins with exceptionally high asymmetric induction.The product alcohols, produced by oxidation of the intermediate organoboranes, exhibit enantiomeric purities in the range of 53-100percent ee and reveal the same absolute configuration.Enantiomeric purities of the products increase with increasing steric requirements of the alkyl or phenyl substituent in the trans-disubstituted or trisubstituted alkene.

Monoisopinocampheylborane: An Excellent Chiral Hydroborating Agent for Phenyl-Substituted Tertiary Olefins. Synthesis of Alcohols Approaching 100percent Enantiomeric Excess

Monoisopinocampheylborane (IPCBH2), a less hindered chiral hydroborating agent, is highly effective for the hydroboration of phenyl-substituted tertiary olefins, such as 1-phenyl-1-cyclopentene, 1-phenyl-1-cyclohexene, (E)- and (Z)-2-phenyl-2-butenes, and