1517-59-5

Usage

Also known as

2-Methyl-2-phenyl-1-propanol, S-(+)-2-Methyl-2-phenyl-1-propanol
Organic compound
Commonly used in the production of pharmaceuticals and fragrances
Colorless liquid
Floral, rose-like odor
Used as a fragrance ingredient in perfumes, soaps, and personal care products
Used as a chiral auxiliary in asymmetric synthesis
Used as a chiral resolving agent for carboxylic acids
Potential applications in the production of pharmaceutical drugs and fine chemicals due to its chiral properties.

Upstream product

• 1078-58-6 diphenylzinc 
• 529-20-4 2-methylphenyl aldehyde 
• 16419-60-6 2-Methylphenylboronic acid 
• 100-52-7 benzaldehyde 
• 38111-44-3 phenylzinc(II) bromide 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 131-58-8 2-Methylbenzophenone 
• 98-80-6 phenylboronic acid 
• 3262-89-3 triphenylboroxine 
• 262439-60-1 2-[(S)-(2-Bromo-phenyl)-phenyl-methoxy]-tetrahydro-pyran 
• 143880-86-8 (S)-o-bromobenzhydrol 
• 7294-50-0 tri-o-tolylboroxine 
• 100-58-3 phenylmagnesium bromide 
• 71-43-2 benzene 

Downstream Products

• 33425-91-1 (R)-N,N-dimethyl-N-{2-[1-(2-methylphenyl)-1-phenylmethoxy]ethyl}amine 

Relevant academic research and scientific papers

Tridentate nitrogen phosphine ligand containing arylamine NH as well as preparation method and application thereof

The invention discloses a tridentate nitrogen phosphine ligand containing arylamine NH as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The tridentate nitrogen phosphine ligand disclosed by the invention is the first case of tridentate nitrogen phosphine ligand containing not only a quinoline amine structure but also chiral ferrocene at present, a noble metal complex of the type of ligand shows good selectivity and extremely high catalytic activity in an asymmetric hydrogenation reaction, meanwhile, a cheap metal complex of the ligand can also show good selectivity and catalytic activity in the asymmetric hydrogenation reaction, and is very easy to modify in the aspects of electronic effect and space structure, so that the ligand has huge potential application value. A catalyst formed by the ligand and a transition metal complex can be used for catalyzing various reactions, can be used for synthesizing various drugs, and has important industrial application value.

Amino Acid-Functionalized Metal-Organic Frameworks for Asymmetric Base–Metal Catalysis

We report a strategy to develop heterogeneous single-site enantioselective catalysts based on naturally occurring amino acids and earth-abundant metals for eco-friendly asymmetric catalysis. The grafting of amino acids within the pores of a metal-organic framework (MOF), followed by post-synthetic metalation with iron precursor, affords highly active and enantioselective (>99 % ee for 10 examples) catalysts for hydrosilylation and hydroboration of carbonyl compounds. Impressively, the MOF-Fe catalyst displayed high turnover numbers of up to 10 000 and was recycled and reused more than 15 times without diminishing the enantioselectivity. MOF-Fe displayed much higher activity and enantioselectivity than its homogeneous control catalyst, likely due to the formation of robust single-site catalyst in the MOF through site-isolation.

A Cobalt(II) Complex Bearing the Amine(imine)diphosphine PN(H)NP Ligand for Asymmetric Transfer Hydrogenation of Ketones

Novel chiral cobalt complex a containing amine(imine)diphosphine PN(H)NP ligand and complex b containing bis(amine)diphosphine PN(H)N(H)P ligand were synthesized. The structures of two complexes were characterized by X-ray crystallography and high resolution mass spectrometry. The catalytic performances of cobalt complexes a and b for asymmetric transfer hydrogenation (ATH) of ketones under mild conditions were evaluated using 2-propanolisopropanol as solvent and hydrogen source after being activated by 8 equivalents of base. Complex a showed a good reactivity for reduction of ketones, with a turnover number (TON) of up to 555, and a maximum enantiomeric excess (ee) value of up to 91 %. Complex b exhibited inertness for hydrogenation of ketones. Electronic structure studies on a and b were conducted to account for the function of ligands on the catalytic performances.

Manganese catalyzed asymmetric transfer hydrogenation of ketones

The asymmetric transfer hydrogenation (ATH) of a wide range of ketones catalyzed by manganese complex as well as chiral PxNy-type ligand under mild conditions was investigated. Using 2-propanol as hydrogen source, various ketones could be enantioselectively hydrogenated by combining cheap, readily available [MnBr(CO)5] with chiral, 22-membered macrocyclic ligand (R,R,R',R')-CyP2N4 (L5) with 2 mol% of catalyst loading, affording highly valuable chiral alcohols with up to 95% ee.

Chiral Iron(II)-Catalysts within Valinol-Grafted Metal-Organic Frameworks for Enantioselective Reduction of Ketones

The development of highly efficient and enantioselective heterogeneous catalysts based on earth-abundant elements and inexpensive chiral ligands is essential for environment-friendly and economical production of optically active compounds. We report a strategy of synthesizing chiral amino alcohol-functionalized metal-organic frameworks (MOFs) to afford highly enantioselective single-site base-metal catalysts for asymmetric organic transformations. The chiral MOFs (vol-UiO) were prepared by grafting of chiral amino alcohol such as l-valinol within the pores of aldehyde-functionalized UiO-MOFs via formation of imine linkages. The metalation of vol-UiO with FeCl2 in THF gives amino alcohol coordinated octahedral FeII species of vol-FeCl(THF)3 within the MOFs as determined by X-ray absorption spectroscopy. Upon activation with LiCH2SiMe3, vol-UiO-Fe catalyzed hydrosilylation and hydroboration of a range of aliphatic and aromatic carbonyls to afford the corresponding chiral alcohols with enantiomeric excesses up to 99%. Vol-UiO-Fe catalysts have high turnover numbers of up to 15 ?000 and could be reused at least 10 times without any loss of activity and enantioselectivity. The spectroscopic, kinetic, and computational studies suggest iron-hydride as the catalytic species, which undergoes enantioselective 1,2-insertion of carbonyl to give an iron-alkoxide intermediate. The subsequent σ-bond metathesis between Fe-O bond and Si-H bond of silane produces chiral silyl ether. This work highlights the importance of MOFs as the tunable molecular material for designing chiral solid catalysts based on inexpensive natural feedstocks such as chiral amino acids and base-metals for asymmetric organic transformations.

Binaphthyl-prolinol chiral ligands: Design and their application in enantioselective arylation of aromatic aldehydes

Binaphthyl-prolinol ligands were designed and applied in enantioselective arylation of aromatic aldehydes and sequential arylation-lactonization of methyl 2-formylbenzoate. Under optimized conditions, the reactions provided the desired diarylmethanols and 3-aryl phthalides in up to 96% yields with up to 99% ee and up to 89% yields with up to 99% ee, respectively. In particular, essentially optically pure 3-aryl phthalides (over 99% ee) were obtained in large quantities through recrystallization. This journal is

Method for synthesizing chiral secondary alcohol compound

The invention discloses a method for synthesizing a chiral secondary alcohol compound. The method comprises the following step of: reacting a ketone compound in an aprotic organic solvent at room temperature and inert gas atmosphere under the action of a chiral cobalt catalyst and an activating agent by taking a combination of bis(pinacolato)diboron and alcohol or water as a reducing agent to obtain the chiral secondary alcohol compound. According to the method disclosed by the invention, a combination of pinacol diborate and alcohol or water which are cheap, stable and easy to obtain is taken as a reducing agent, and a ketone compound is efficiently reduced to synthesize a corresponding chiral secondary alcohol compound in an aprotic organic solvent under the action of a chiral cobalt catalyst; in a chiral cobalt catalyst adopted by the method, when a chiral ligand is PAOR, an activating agent is NaBHEt3 or NaOtBu and an adopted raw material is aromatic ketone, the yield is 80% or above, and the optical purity is 90% or above; and when the adopted raw material is alkane ketone, the yield can reach 70% or above, and the optical purity can reach 80% or above.

Enantioselective Si-H Insertion Reactions of Diarylcarbenes for the Synthesis of Silicon-Stereogenic Silanes

We report the first example of enantioselective, intermolecular diarylcarbene insertion into Si-H bonds for the synthesis of silicon-stereogenic silanes. Dirhodium(II) carboxylates catalyze an Si-H insertion using carbenes derived from diazo compounds where selective formation of an enantioenriched silicon center is achieved using prochiral silanes. Fourteen prochiral silanes were evaluated with symmetrical and prochiral diazo reactants to produce a total of 25 novel silanes. Adding an ortho substituent on one phenyl ring of a prochiral diazo enhances enantioselectivity up to 95:5 er with yields up to 98percent. Using in situ IR spectroscopy, the impact of the off-cycle azine formation is supported based on the structural dependence for relative rates of diazo decomposition. A catalytic cycle is proposed with Si-H insertion as the rate-determining step, supported by kinetic isotope experiments. Transformations of an enantioenriched silane derived from this method, including selective synthesis of a novel sila-indane, are demonstrated.

Palladium-Catalyzed Intramolecular Mizoroki-Heck-Type Reaction of Diarylmethyl Carbonates

A palladium-catalyzed intramolecular Mizoroki-Heck-type reaction of diarylmethyl tert-butyl carbonates has been developed. The reaction proceeds under external base-free, neutral conditions to form the corresponding methyleneindanes in good yields only with liberation of CO2 and tBuOH. The resulting exo-methylene moiety is reactive and thus a good synthetic handle for further manipulations. Additionally, the asymmetric synthesis is also possible through a Pd/chiral Mandyphos ligand-mediated kinetic resolution. To the best of our knowledge, this is the first successful example of catalytic enantioselective Mizoroki-Heck-type reaction of secondary benzyl electrophiles. (Figure presented.).

Isosterically designed chiral catalysts: Rationale, optimization and their application in enantioselective nucleophilic addition to aldehydes

Proline-based N,N′-dioxide ligands were designed on the basis of isosteric approach, and were successfully applied in enantioselective nucleophilic addition to aldehydes. In the presence of 10 mol% of chiral ligand 1b, enantioselective addition of diethylzinc to aldehydes provided the corresponding secondary alcohols in up to 90% isolated yield and up to 99% ee. Similarly, using 3e as chiral ligand, enantioselective arylation and alkynylation of aldehydes also proceeded readily, leading to the desired chiral alcohols in up to 92% isolated yield at 99% ee and 80% isolated yields and up to 84% ee, respectively. The current work would shed light on expanding the structure diversity in the design of chiral ligands and chiral catalysts.