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Upstream product

• 1078-58-6 diphenylzinc 
• 590-86-3 isovaleraldehyde 
• 78-77-3 Isobutyl bromide 
• 100-52-7 benzaldehyde 
• 98-80-6 phenylboronic acid 
• 217455-89-5 (3-methyl-1-chlorobutyl)benzene 
• 100-51-6 benzyl alcohol 
• 26382-04-7 diisopropyl-carbamic acid phenylmethyl ester 
• 145429-22-7 2-isobutyl-5,5-dimethyl-1,3,2-dioxaborinane 
• 1344196-49-1 (i-Bu)Ti(O-i-Pr)3 
• 1338246-58-4 (R)-4,4,5,5-tetramethyl-2-(3-methyl-1-phenylbutyl)-1,3,2-dioxaborolane 
• 582-62-7 3-methyl-1-phenylbutan-1-one 
• 1565-86-2 3-Methyl-1-phenyl-1-butanol 
• 97-72-3 2-Methylpropionic anhydride 

Relevant academic research and scientific papers

Chiral oxazaborolidines bearing a 1- or 2-naphthylmethyl group as catalysts for the enantioselective borane reduction of ketones: Experimental and quantum chemical calculations

Two new catalysts for the enantioselective reduction of ketones, chiral 1,3,2-oxazaborolidines substituted at carbon 4 by a 1- or 2-naphthylmethyl group, have been prepared from the related amino alcohols, by treatment with borane in tetrahydrofuran, and

Asymmetric reduction of aromatic ketones in pyridinium-based ionic liquids

The asymmetric reduction of aromatic ketones has been studied in pyridinium-based room temperature ionic liquids, namely, 1-ethyl-pyridinium tetrafluoroborate, [EtPy]+[BF4]- and 1-ethyl-pyridinium trifluoroacetate, [EtPy]

Mechanistic insights into the phosphine-free RuCp*-diamine-catalyzed hydrogenation of aryl ketones: Experimental and theoretical evidence for an alcohol-mediated dihydrogen activation

The commercially available chiral diamine quincorine-amine, originally derived from quinine, was found to be a highly active catalyst for ruthenium-catalyzed hydrogenation of ketones. The complex formed between the quincorine-amine, containing both a prim

Novel Chiral PNNP Ligands with a Pyrrolidine Backbone – Application in the Fe-Catalyzed Asymmetric Transfer Hydrogenation of Ketones

The PNNP ligand (R,R)-{PPh2(2-C6H4)CH=N(pyrrolidine-NBn)-}2 2 was prepared by condensation between 2-diphenylphosphino benzaldehyde and the pyrrolidine-substituted diamine 1. Reduction with NaBH4 in MeOH afforded (R,R)-{PPh2(2-C6H4)CH–NH(pyrrolidine-NBn)-}2 3. The corresponding iron(II) complexes [FeCl2(2)] (4), [Fe(CH3CN)2(2)](BF4)2 (5) and [Fe(CH3CN)2(2)](PF6)2 (6) were synthesized and fully characterized by NMR, ESI-HRMS, and EA. DFT calculations for complexes [FeCl2(2)] (4) and [Fe(CH3CN)2(2)](BF4)2 (5) were carried out in order to investigate the stability of related structures. The PNNP ligands 2 and 3 in combination with Fe3(CO)12 as iron source were tested as catalysts in the asymmetric transfer hydrogenation of a variety of ketones with conversions higher than 95 % and enantioselectivities up to 97 %.

Performance of Recombinant-Whole-Cell-Catalyzed Reductions in Deep-Eutectic-Solvent-Aqueous-Media Mixtures

Deep-eutectic solvents (DES) are cost-effective, nonhazardous solvents that may be used in biocatalysis as nonconventional media that enable biotransformations with industrially sound high substrate loadings. Based on promising prognoses, this paper explo

Copper(I)-Catalyzed Enantioconvergent Borylation of Racemic Benzyl Chlorides Enabled by Quadrant-by-Quadrant Structure Modification of Chiral Bisphosphine Ligands

The first copper(I)-catalyzed enantioselective borylation of racemic benzyl chlorides has been realized by a quadrant-by-quadrant structure modulation of QuinoxP*-type bisphosphine ligands. This reaction converts racemic mixtures of secondary benzyl chlorides into the corresponding chiral benzylboronates with high enantioselectivity (up to 92 % ee). The results of mechanistic studies suggest the formation of a benzylic radical intermediate. The results of DFT calculations indicate that the optimal bisphosphine-copper(I) catalyst engages in noncovalent interactions that efficiently recognize the radical intermediate, and leads to high levels of enantioselectivity.

Nickel-Catalyzed Enantioconvergent Borylation of Racemic Secondary Benzylic Electrophiles

Nickel-catalyzed cross-coupling has emerged as the most versatile approach to date for achieving enantioconvergent carbon–carbon bond formation using racemic alkyl halides as electrophiles. In contrast, there have not yet been reports of the application of chiral nickel catalysts to the corresponding reactions with heteroatom nucleophiles to produce carbon–heteroatom bonds with good enantioselectivity. Herein, we establish that a chiral nickel/pybox catalyst can borylate racemic secondary benzylic chlorides to provide enantioenriched benzylic boronic esters, a highly useful family of compounds in organic synthesis. The method displays good functional group compatibility (e.g., being unimpeded by the presence of an indole, a ketone, a tertiary amine, or an unactivated alkyl bromide), and both of the catalyst components (NiCl2?glyme and the pybox ligand) are commercially available.

Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes

The Brook rearrangement of simple, chiral tertiary benzylic α-hydroxysilanes is presented. The rearrangement followed by proton trapping is enantiospecific and proceeds with inversion of the configuration at the carbon center. Importantly, the [1,2]-Brook

Chiral thiophosphoramide catalyzed asymmetric aryl transfer reactions for the synthesis of functional diarylmethanols

In this investigation, chiral thiophosphoramide 3d was easily prepared from chiral (1R,2R)-1,2-diphenylethylenediamine and then applied as an efficient chiral ligand in the catalytic asymmetric arylation reactions of various aromatic aldehydes. The corresponding diarylmethanol products were produced with good to excellent yields (up to 98%) and enantioselectivities (up to 94%). The recovery of chiral ligand 3d could be as high as 96%.

Third-Generation Amino Acid Furanoside-Based Ligands from d-Mannose for the Asymmetric Transfer Hydrogenation of Ketones: Catalysts with an Exceptionally Wide Substrate Scope

A modular ligand library of α-amino acid hydroxyamides and thioamides was prepared from 10 different N-tert-butyloxycarbonyl-protected α-amino acids and three different amino alcohols derived from 2,3-O-isopropylidene-α-d-mannofuranoside. The ligand library was evaluated in the half-sandwich ruthenium- and rhodium-catalyzed asymmetric transfer hydrogenation of a wide array of ketone substrates, including simple as well as sterically demanding aryl alkyl ketones, aryl fluoroalkyl ketones, heteroaromatic alkyl ketones, aliphatic, conjugated and propargylic ketones. Under the optimized reaction conditions, secondary alcohols were obtained in high yields and in enantioselectivities up to >99%. The choice of ligand/catalyst allowed for the generation of both enantiomers of the secondary alcohols, where the ruthenium-hydroxyamide and the rhodium-thioamide catalysts act complementarily towards each other. The catalytic systems were also evaluated in the tandem isomerization/asymmetric transfer hydrogenation of racemic allylic alcohols to yield enantiomerically enriched saturated secondary alcohols in up to 98% ee. Furthermore, the catalytic tandem α-alkylation/asymmetric transfer hydrogenation of acetophenones and 3-acetylpyridine with primary alcohols as alkylating and reducing agents was studied. Secondary alcohols containing an elongated alkyl chain were obtained in up to 92% ee. (Figure presented.).