257298-92-3

Basic information

• Product Name: (R)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane
• Synonyms: (R)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane
• CAS NO: 257298-92-3
• Molecular Weight: 232.131
• Mol File: 257298-92-3.mol

Chemical Properties

• CAS DataBase Reference: (R)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane(257298-92-3)
• EPA Substance Registry System: (R)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane(257298-92-3)

Safety Data

• Hazardous Substances Data: 257298-92-3(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 73183-34-3 bis(pinacol)diborane 
• 133038-72-9 (R)-N,N-diisopropyl O-(1-phenyl)ethylcarbamate 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 14900-39-1 phenylvinylboronic acid 
• 672-65-1 (1-chloroethyl)benzene 
• 57199-00-5 2,4,6-triisopropylbenzoyl chloride 
• 143825-84-7 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 156575-60-9 2-(1-phenyl-ethyl)-benzo[1,3,2]dioxaborole 
• 174090-36-9 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane 

Downstream Products

• 257298-97-8 2-((R)-1-Chloro-2-phenyl-propyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 1190868-57-5 (2R)-2-phenyl-1-(4-(trifluoromethyl)phenyl)propan-1-ol 
• 184888-43-5 (R)-(1-phenylethyl)carbamic acid tert-butyl ester 
• 147169-48-0 (S)-tert-butyl 1-phenylethylcarbamate 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 

Relevant articles and documents

Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes

The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2 is crucial for ensuring fast transmetalation to achieve high enantioselectivities.

Ring-Opening Lithiation–Borylation of 2-Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters

Stereogenic trifluoromethyl-substituted carbon centers are highly sought-after moieties in pharmaceutical and agrochemical discovery. Here, we show that lithiation–borylation reactions of 2-trifluoromethyl oxirane give densely functionalized and highly versatile trifluoromethyl-substituted α-tertiary boronic esters. The intermediate boronate complexes undergo the desired 1,2-rearrangement of the carbon-based group with complete retentive stereospecificity, a process that was only observed in non-polar solvents in the presence of TESOTf. Although the trifluoromethyl group adversely affects subsequent transformations of the α-boryl group, Zweifel olefinations provide trifluoromethyl-bearing quaternary stereocenters substituted with alkenes, alkynes and ketones.

Efficient Access to Chiral β-Borylated Carboxylic Esters via Rh-Catalyzed Hydrogenation

Rh/bisphosphine?thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydrogenation of (Z)-β-substituted-β-boryl-α,β-unsaturated esters was successfully developed, furnishing a variety of chiral β-borylated carboxylic esters with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). The gram-scale asymmetric hydrogenation was performed efficiently in the presence of only 0.05 mol% (S/C=2 000) catalyst loading with full conversion, 99% yield and 99% ee. Moreover, the hydrogenation product was easily converted to other versatile synthetic intermediates, such as methyl (S)-3-hydroxy-3-phenylpropanoate and methyl (S)-3-(furan-2-yl)-3-phenylpropanoate. (Figure presented.).

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.

Ir/Thioether-Carbene, -Phosphinite, and -Phosphite Complexes for Asymmetric Hydrogenation. A Case for Comparison

We studied for the first time the potential of novel and simple Ir/thioether-NHC complexes in the asymmetric hydrogenation of unfunctionalized olefins and cyclic β-enamides. For comparison, we prepared and applied the analogues thioether-phosphinite/phosphite complexes. We found that the efficiency of the new Ir/thioether-NHC catalyst precursors varies with the type of olefin. Thus, while the Ir/thioether-NHC catalyst precursors provided lower catalytic performance than their related Ir/thioether-P complexes in the hydrogenation of olefins lacking a coordinating group, the catalysts had similar good performance for the reduction of functionalized olefins (e.g., tri- and disubstituted enol phosphonate derivatives). Catalytic results together with the studies of the reactivity toward H2 indicated that the thioether-carbene design favors the formation of inactive trinuclear species, which are responsible for the low activities obtained with these carbene-type catalysts. Nevertheless, this catalyst deactivation can be avoided by using functionalized olefins such as enol phosphonates. We also report the discovery of simple-to-synthesize Ir/thioether-P catalysts containing a simple backbone that gave high enantioselectivities for some trisubstituted olefins, some challenging 1,1′-disubstituted olefins, and cyclic β-enamides.

Cobalt-Catalyzed Asymmetric Markovnikov Hydroboration of Styrenes

A cobalt-catalyzed asymmetric hydroboration of styrenes using an imidazoline phenyl picoliamide (ImPPA) ligand was first reported to deliver the valuable chiral secondary organoboronates with good functional tolerance and high enantioselectivity (up to >9

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.

Pyrrolidine-Based P,O Ligands from Carbohydrates: Easily Accessible and Modular Ligands for the Ir-Catalyzed Asymmetric Hydrogenation of Minimally Functionalized Olefins

The potential of P,O-iminosugar based ligands in the Ir-catalyzed asymmetric hydrogenation of minimally functionalized olefins is presented. These new ligands were prepared from easily available carbohydrates (D-mannose, D-ribose and D-arabinose). The stereochemical and polyfunctional diversity of carbohydrates allowed the modulation of the ligands, both from their electronic properties and the rigidity of their backbone. High enantioselectivities (ee’s up to 99 %) can be reached in the hydrogenation of selected tri- and disubstituted substrates.

Compound containing chiral imidazole picolinamide as well as preparation method and application thereof

The invention discloses a compound containing chiral imidazole picolinamide. The compound is shown as a formula (I). The invention further discloses a preparation method and application of the compound containing chiral imidazole picolinamide. The compoun

Chiral quinoline amine compound and preparation method and application thereof

The invention discloses a chiral quinoline amine compound shown in a formula (1), and discloses a simple preparation method convenient to implement. The quinoline amine shown in the formula (1) can beused for preparing a chiral organic boron ester compound. A chiral oxazoline or imidazoline base quinoline amine compound and a transition metal MY'n in-situ complex can be adopted as a homogeneous catalyst, the catalyst is subjected to asymmetry hydroboration addition on carbon-carbon atom double bonds of the prochirality organic compound to be used for preparing the chiral organic boron compound, and the prochirality unsaturated compound for optimizing the asymmetric boron hydrogen effect is a styrene compound. The prepared chiral organic boron ester compound is an important organic synthesis midbody and is particularly applied to the production aspect of medicine preparations, spice, fumet and agricultural chemicals.