23406-60-2

Upstream product

• 13491-13-9 (R)-2-isopropyl-2-phenylacetic acid 
• 90499-41-5 2-phenyl-3-methylbutanol 
• 78019-45-1 (S)-(E)-4-Phenyl-5-methyl-2-hexene 
• 1325729-44-9 (R)-4,4,5,5-tetramethyl-2-(3-methyl-2-phenylbutyl)-1,3,2-dioxaborolane 
• 81176-43-4 (S)-trans-4-phenyl-3-buten-2-ol 
• 38082-08-5 3-methyl-2-phenyl-but-1-en-1-one 
• 865363-55-9 (R)-3-Methyl-2-phenyl-butyric acid 2,2-diphenyl-vinyl ester 
• 1888-75-1 isopropyllithium 
• 20780-54-5 (S)-styrene oxide 
• 143838-44-2 methyl (R)-3-methyl-2-phenylbutanoate 
• 108-22-5 Isopropenyl acetate 
• 586341-97-1 (3R,4E)-2-methyl-3-phenylhex-4-enoic acid 
• 586341-98-2 (3R,4E)-2-methyl-3-phenylhex-4-en-1-ol 

Downstream Products

• 143770-77-8 (R)-1-acetoxy-3-methyl-2-phenylbutane 
• 74669-75-3 (R)-3-Methyl-2-phenylbutylazid 
• 67152-34-5 (R)-3-Methyl-2-phenylbutyltosylat 
• 196106-01-1 (R)-3-methyl-2-phenylbutan-1-amine 

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.).

NHC-Cu-catalyzed enantioselective hydroboration of acyclic and exocyclic 1,1-disubstituted aryl alkenes

Tough nut to crack: Chiral bidentate N-heterocyclic carbene copper complexes were designed that promote enantioselective hydroborations of one of the most difficult substrate classes: acyclic and exocyclic 1,1-disubstituted alkenes undergo reaction with >98% site selectivity, in up to >98% yield and e.r=96.5:3.5 (see scheme, B2(pin)2 = bis(pinacolato)diboron). Copyright

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.

A general approach towards 2-substituted 3-hydroxy propanoates; application to the synthesis of methyl tropinate

Enantiomerically pure R or S 2-substituted 3-hydroxy propanoates may be prepared by regioselective BF3 promoted opening of homochiral styrene oxide by lithium cyanocuprates followed by oxidative cleavage of the aromatic moiety with catalytic ru

Lipase-catalyzed enantioselective acylation of alcohols: A predictive active site model for lipase YS to identify which enantiomer of an alcohol reacts faster in this acylation

Primary alcohols having a hydroxymethyl group at an S sterogemic center and secondary alcohols with an R configuration are preferentially acylated to give the corresponding acetates by lipase YS (from Pseudomonas fluorescens)-catalyzed acylation using isopropenyl acetate as the acylating agent in diisopropyl ether. On the basis of enantiomer selectivities observed, a predictive active site model for lipase YS is proposed for identifying which enantiomer of a primary or a secondary alcohol reacts faster in this acylation.

Lipase YS-catalysed Acylation of Alcohols: a Predictive Active Site Model for Lipase YS to Identify which Enantiomer of a Primary or a Secondary Alcohol Reacts Faster in this Acylation

Primary alcohols having a hydroxymethyl group at an S chiral centre and secondary alcohols with an R configuration are preferentially acylated to give the corresponding acetates by lipase YS-catalysed acylation in diisopropyl ether; a predictive cubic-spaced active site model for lipase YS is proposed for identifying which enantiomer of a primary or a secondary alcohol reacts faster in this acylation.

Stereochemistry of Aliphatic Carbocations, 15. Rearrangements in 2-Arylalkyl Systems

Phenyl shifts from secondary to primary carbon proceed with virtually complete inversion at the migration origin, regardless whether they are induced by solvolysis of the aryl sulfonate 25 or by deamination of the amines 12, 17, 26, and 43.Sequential rearrangements (Ph, CH3 and Ph, H) are likewise stereo- and regiospecific.These results strongly support the intervention of phenonium ions.In contrast, the competitive alkyl shifts (deamination only) from benzylic to primary carbon produce but a small excess of inversion (Me 27percent, Et 13percent, iPr 20percent, tBu 3percent).Obviously, benzyl cations are the predominant intermediates.