16460-75-6

Upstream product

• 4286-15-1 (S)-2-phenylbutyric acid 
• 938-79-4 (2R)-2-phenylbutanoic acid 
• 106-88-7 (R)-(+)-1,2-epoxybutane 
• 71-43-2 benzene 
• 108-22-5 Isopropenyl acetate 
• 2035-94-1 2-phenylbutan-1-ol 
• 109686-82-0 RS-2-phenylbutyrate 
• 104499-21-0 (4R,5S)-3-<(2R)-phenylbutanoyl>-4-methyl-5-phenyl-1,3-oxazolidine-2-thione 
• 159345-11-6 (S)-N-((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-2-phenyl-butyramide 
• 42307-60-8 (S)-2-methylbutanal 
• 2439-43-2 (2RS)-2-phenylbutanal 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 1325729-42-7 (R)-(+)-4,4,5,5-tetramethyl-2-(2-phenylbutyl)-1,3,2-dioxaborolane 
• 123-20-6 vinyl n-butyrate 

Downstream Products

• 33204-52-3 (2R)-cyclohexyl-1-butanol 
• 1195590-62-5 (S)-heptan-3-ylbenzene 
• 1043500-12-4 ((R)-1-iodomethyl-propyl)benzene 
• 1043495-96-0 (4S)-4-((2S)-2-phenylbutyl)-4,5-dihydro-1,3-oxazol-2-ylamine 
• 1043500-14-6 (2R,5S)-2-isopropyl-3,6-dimethoxy-5-((S)-2-phenylbutyl)-2,5-dihydropyrazine 
• 1043500-17-9 (2S,4S)-2-amino-4-phenylhexanoic acid methyl ester 
• 1043500-22-6 (2S,4S)-2-amino-4-phenylhexan-1-ol 
• 26798-31-2 (-)-2-Phenyl-1-butyl-α-naphthylcarbamat 
• 20068-14-8 (+)-(S)-1-Chlor-2-phenyl-butan 

Relevant academic research and scientific papers

DIFFERENCES IN REACTIVITY AND ENANTIOSELECTIVITY IN LIPASE REACTIONS WITH CARBOXYLIC ESTERS AND ALCOHOLS BEARING THE SAME STEREOGENIC CENTER

The reaction rate and stereochemical outcome of lipase reactions obtained with carboxylic esters and alcohols, which contain the same stereogenic center, can be modulated by changing the mode of the lipase reaction, i.e. ester hydrolysis versus alcohol acetylation.

Highly Enantioselective Catalytic Kinetic Resolution of α-Branched Aldehydes through Formal Cycloaddition with Homophthalic Anhydrides

A new catalytic methodology was developed to promote an efficient one-pot kinetic resolution of racemic aldehydes with selectivity (s*) of up to 91 (99:1 d.r., >99 % ee) in a cycloaddition reaction with enolizable anhydrides to afford dihydroisocoumarin products (a core prevalent in natural products and molecules of medicinal interest) containing three contiguous stereocentres.

MANGANESE-CATALYSED HYDROGENATION OF ESTERS

The present invention relates to the field of catalytic hydrogenation and, more particularly, to methods of manganese-catalysed hydrogenation of esters to alcohols. Advantageously, where the esters are chiral, the hydrogenations proceed with high or complete stereochemical integrity..

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.).

Manganese Catalyzed Hydrogenation of Enantiomerically Pure Esters

A manganese-catalyzed hydrogenation of esters has been accomplished with TONs up to 1000, using cheap, environmentally benign, potassium carbonate and simple alcohols as activator and solvent, respectively. The weakly basic conditions lead to good functional group tolerance and enable the hydrogenation of enantiomerically enriched α-chiral esters with essentially no loss of stereochemical integrity.

Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem-Diborylalkanes by an Asymmetric Allylic Substitution

We report the successful generation of (diborylmethyl)zinc(II) species by transmetallation beteween isolable (diborylmethyl)lithium and zinc(II) halide (X=Br, Cl) and their application in the synthesis of enantioenriched gem-diborylalkanes bearing a stereogenic center at the β-position of the diboryl groups by an asymmetric allylic substitution reaction. The reaction has a broad substrate scope, and various enantioenriched gem-diborylalkanes can be obtained in good yields with excellent enantioselectivity. Further elaboration of the enantioenriched gem-diborylalkanes provides access to a diverse set of valuable chiral building blocks.

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates

Diastereoselective radical coupling was achieved with chiral auxiliaries. The radicals were generated by anodic decarboxylation of five malonic acid derivatives. These were prepared from benzyl malonates and four menthol auxiliaries. Coelectrolyses with 3,3-dimethylbutanoic acid in methanol at platinum electrodes in an undivided cell afforded hetero-coupling products in 22-69% yield with a diastereoselectivity ranging from 5 to 65% de. Electrolyses without a coacid led to diastereomeric homo-coupling products in 21-50% yield with ratios of diastereomers being 1.17:2.00:0.81 to 7.03:2.00. The stereochemistry of the new stereogenic centers was confirmed by X-ray structure analysis and 13C NMR data.

Impact of variation of the acyl group on the efficiency and selectivity of the lipase-mediated resolution of 2-phenylalkanols

By tuning the steric properties of the acyl group to control the efficiency and selectivity of the resolution, 2-phenyl-1-propanol 1a was prepared by lipase-catalysed hydrolysis using a short-chain acyl group, with E-values of up to 66 (ee up to 95%). 2-Phenylbutan-1-ol 1b was similarly resolved (up to 86% ee) using the optimised conditions, while the ester of the more sterically demanding 3-methyl-2-phenylbutan-1-ol 1c proved resistant to enzymatic hydrolysis under these conditions.

Synthesis and Antibacterial Activity of Four Stereoisomers of the Spider-Pathogenic Fungus Metabolite Torrubiellone D

Four stereoisomers of the spider-pathogenic fungus metabolite torrubiellone D were synthesized for the first time in 10% overall yield starting from l-tyrosine or d-tyrosine. The 3-decatrienoyl side chain was assembled and attached via (E)-selective HWE and Wittig olefinations. Their antibiotic activities against drug-susceptible Escherichia coli strains differed considerably.

Discovery and Characterization of 2-Aminooxazolines as Highly Potent, Selective, and Orally Active TAAR1 Agonists

2-Aminooxazolines were discovered as a novel structural class of TAAR1 ligands. Starting from a known adrenergic compound 1, structural modifications were made to obtain highly potent and selective TAAR1 ligands such as 12 (RO5166017), 18 (RO5256390), 36 (RO5203648), and 48 (RO5263397). These compounds exhibit drug-like physicochemical properties, have good oral bioavailability, and display in vivo activity in a variety of animal models relevant for psychiatric diseases and addiction.