19643-71-1

Upstream product

• 13490-69-2 (S)-2-phenyl-3-methylbutyric acid 
• 90499-41-5 2-phenyl-3-methylbutanol 
• 172424-32-7 Acetic acid (S)-3-methyl-2-phenyl-butyl ester 
• 865363-45-7 (S)-3-Methyl-2-phenyl-butyric acid 2,2-diphenyl-vinyl ester 
• 591-51-5 phenyllithium 
• 586341-95-9 (3S,4E)-2-methyl-3-phenylhex-4-enoic acid 
• 586341-96-0 (3S,4E)-2-methyl-3-phenylhex-4-en-1-ol 
• 38082-08-5 3-methyl-2-phenyl-but-1-en-1-one 
• 2439-44-3 3-methyl-2-phenylbutanal 
• 222021-01-4 {(R)-1-[(2R,5S)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidenemethyl]-2-methyl-propyl}-benzene 
• 78019-48-4 (2E,4R)-5-methyl-4-phenylhex-2-ene 
• 108-22-5 Isopropenyl acetate 
• 19079-80-2 ethyl (S)-3-methyl-2-phenylbutanoate 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 

Downstream Products

• 36667-54-6 (-)-S-5-Phenyl-6-methyl-1-hepten 
• 36667-53-5 (-)-S-4-Phenyl-5-methyl-1-hexen 
• 106498-32-2 (S)-3-methyl-2-phenylbutylamine 
• 36617-73-9 (+'-(S)-1-Chlor-2-phenyl-3-methyl-butan 

Relevant academic research and scientific papers

Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst

Evaluation of an esterase annotated as 26D isolated from a marine metagenomic library is described. Esterase 26D was found to have a unique substrate scope, including synthetic transformations which could not be readily effected in a synthetically useful manner using commercially available enzymes. Esterase 26D was more selective towards substrates which had larger, more sterically demanding substituents (i. e. iso-propyl or tert-butyl groups) on the β-carbon, which is in contrast to previously tested commercially available enzymes which displayed a preference for substrates with sterically less demanding substituents (e.g. methyl group) at the β-carbon. (Figure presented.).

Determination of the Absolute Configuration of β-Chiral Primary Alcohols Using the Competing Enantioselective Conversion Method

A method for determining the absolute configuration of β-chiral primary alcohols has been developed. Enantioenriched alcohols were acylated in the presence of either enantiomer of the enantioselective acylation catalyst HBTM, and the faster reaction was determined by measuring product conversion using 1H NMR spectroscopic analysis. An empirical mnemonic was developed that correlates the absolute configuration of the alcohol to the faster reacting catalyst. Successful substrates for this method include primary alcohols that bear a "directing group" on the stereogenic center; directing groups include arenes, heteroarenes, enones, and halides.

Filling the gaps in the challenging asymmetric hydroboration of 1,1-disubstituted alkenes with simple phosphite-based phosphinooxazoline iridium catalysts

We have identified a readily accessible phosphinooxazoline-based phosphite-oxazoline catalytic system, (S)-4-isopropyl-2-{2-[(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite]-phenyl}-2-oxazoline (L1a), that can hydroborate a range of 1,1-disubstituted aryl olefins with high enantioselectivity (up to 94%), excellent yields and perfect regioselectivity. The new phosphite-oxazoline ligands efficiently hydroborate a broader range of olefins than previous phosphinooxazoline ligands. In particular, a wide range of α-tert-butylstyrenes can be hydroborated that bear aryl substituents with different electronic and steric properties, which complements previous results with N-heterocyclic copper catalysts, the only other system reported to date that has achieved these reactions.

Enantioselective α-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis

The enantioselective α-arylation of aldehydes has been accomplished using diaryliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable α-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.

Mesoporous silica nanosphere supported ruthenium catalysts for asymmetric hydrogenation

(Chemical Equation Presented) Chiral Ruthenium-diphosphine-diamine complexes with a siloxy pendant are grafted onto mesoporous silica nanospheres. The resulting supported ruthenium catalysts are highly active for the asymmetric hydrogenation of aromatic ketones to afford chiral secondary alcohols and racemic aryl aldehydes to give chiral primary alcohols (see scheme). This immobilization strategy should be amenable to the design of similar heterogeneous catalysts.

Ru-catalyzed asymmetric hydrogenation of racemic aldehydes via dynamic kinetic resolution: Efficient synthesis of optically active primary alcohols

A highly efficient asymmetric hydrogenation of racemic α-arylaldehydes via dynamic kinetic resolution has been developed by using [RuCl2(SDPs)(diamine)] complexes as catalysts, providing chiral primary alcohols in excellent enantioselectivities. Copyright

Catalytic asymmetric hydrogenation of aldehydes

Racemic α-arylaldehydes provide the corresponding primary alcohols via dynamic kinetic resolution in excellent enantioselectivities and yields upon hydrogenation using a Noyori ruthenium catalyst; for example, the biologically active (S)-enantiomer of the non-steroidal anti-inflammatory drug ibuprofen could be synthesized via catalytic enantioselective hydrogenation of aldehyde 1f followed by oxidation with potassium permanganate in 76% isolated yield and 96: 4 er. The Royal Society of Chemistry.

Catalytic asymmetric couplings of ketenes with aldehydes to generate enol esters

(Chemical Equation Presented) With a little help from the ferrocenyl catalyst ((-)-1), a wide array of α-arylalkanoic acid derivatives can be produced from the catalytic asymmetric coupling of ketenes with aldehydes (see scheme). The enol esters are readily transformed into other useful families of compounds such as carboxylic acids and alcohols.

Enantioselective synthesis of benzylic stereocentres via Claisen rearrangement of enantiomerically pure allylic alcohols: Preparation of (R)- and (S)-3-methyl-2-phenylbutylamine

The Johnson-Claisen rearrangement of enantiopure allylic alcohols in triethylorthopropionate is the key step for the preparation of chiral molecules with benzylic stereogenic carbon atoms bearing an isopropyl moiety. The synthetic procedure is applied to the preparation of (R)- and (S)-3-methyl-2-phenylbutylamine.

Chiral α-substituted carbonyls and alcohols from the S(N)2' displacement of cuprates on chiral carbonates: An alternative to the alkylation of chiral enolates

A highly stereoselective sequence of reactions, based on the anti-selective S(N)2' addition of cuprates to allylic carbonates, transforms alkynes or alkenyl halides into carbonyls having α-chiral centers. The method, which uses menthone as a chiral auxiliary, is a useful alternative to the alkylation of chiral enolates with the added advantage of allowing for the 'alkylation' of sec- and tert-alkyl and aryl groups.