1517-61-9

Usage

Physical state

Colorless solid at room temperature

Odor

Strong and sweet

Uses

Synthesis of pharmaceuticals and agricultural products, chiral auxiliary in asymmetric synthesis, resolving agent for racemic compounds, and scent ingredient in fragrance industry

Safety precautions

Can cause irritation to skin, eyes, and respiratory system if not handled properly.

Upstream product

• 100-52-7 benzaldehyde 
• 703-55-9 1-naphthylmagnesiumbromide 
• 15197-44-1 ((R)-Methyl-naphthalen-1-yl-phenyl-silanyl)-phenyl-methanone 
• 66-77-3 1-naphthaldehyde 
• 98-80-6 phenylboronic acid 
• 66-99-9 β-naphthaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 3262-89-3 triphenylboroxine 
• 7519-87-1 tris(1-naphthyl)boroxine 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 555-54-4 diphenylmagnesium 
• 108-86-1 bromobenzene 
• 112176-15-5 C₁₀H₇Ti(OC₃H₇)3 
• 1078-58-6 diphenylzinc 

Downstream Products

• 134295-68-4 (R)-1-Methoxy-1-(α-naphthyl)-1-phenylmethane 

Relevant academic research and scientific papers

Palladium-Catalyzed Stereospecific Decarboxylative Benzylation of Alkynes

Enantioenriched benzyl esters of propiolic acids undergo highly stereospecific decarboxylative coupling to provide 1,1-diarylethynyl methanes. This sp-sp3 coupling does not require strongly basic conditions or preformed organometallics and prod

Crystal structure studies towards the synthesis and applications of n-heterocyclic carbene-metal complexes derived from [2.2]paracyclophane

The crystal structures of six planar chiral N-heterocyclic carbene (NHC) precursors and one NHC-Rh complex derived from [2.2]paracyclophane were described. The NHC-metal complexes were prepared to examine their catalytic activities toward the Rh-catalyzed

Bio-inspired asymmetric aldehyde arylations catalyzed by rhodium-cyclodextrin self-inclusion complexes

Transition-metal catalysts are powerful tools for carbon-carbon bond-forming reactions that are difficult to achieve using native enzymes. Enzymes that exhibit inherent selectivities and reactivities through host-guest interactions have inspired widesprea

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

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.

P-chirogenic Trost ligands mediated asymmetric hydrogenation of simple ketones

Herein, we report a highly active catalyst system consisting of (Rc,Rc,Rp,Rp)-P-chirogenic Trost ligand and [Ru(C6H6)Cl2]2 for asymmetric hydrogenation of simple ketones, affording the corresponding optically active alcohols in moderate enantioselectivity. A synergetic effect between P- and C-chirogenic centers of the P-chirogenic Trost ligands was observed in this asymmetric hydrogenation process.

Chiral electron-rich PNP ligand with a phospholane motif: Structural features and application in asymmetric hydrogenation

Despite the remarkable reactivity that was achieved by a series of transition-metal catalysts with a PNP type ligand, the electron-rich chiral PNP ligands have still been rarely reported because of the difficulties in synthesis and the nature of air-sensitivity. Herein, we report a novel chiral PNP ligand (Heng-PNP) with both a rigid backbone and a bulky tert-butyl group on the phospholane motif. We successfully obtained its divalent iron complex. The chiral environment of its Ir(III) complex was also discussed with quadrant analysis. This tridentate ligand was applied in iridium-catalyzed asymmetric hydrogenation of challenging diaryl ketones: up to 98% ee and 500 TON are achieved. Computational study showed that the twist of conjugate aryl group in the substrate (induced by the special chiral pocket of Ir/Heng-PNP complex) leads to the energy difference in the enantiodetermining step.

Enantiopure Methyl- A nd Phenyllithium: Mixed (Carb-)Anionic Anisyl Fencholate-Aggregates

Methyl- A nd phenyllithium aggregates with enantiopure anisyl fencholate units form after reaction of organolithium reagent with (+)-anisyl fenchol in hydrocarbon and some ethereal solvents. These carbanionic aggregates are characterized by X-ray crystal analyses and exhibit both 3:1 stoichiometry and distorted cubic Li4O3C1 cores, in which three lithium ions coordinate the carbanion (i.e., methylide or phenylide). These three lithium ions define a Lewis acidic surface (Li3), binding the carbanion and expanding with the steric demand of the carbanion (i.e., from Me: 2.62 ?2, over n-Bu: 2.65 ?2 (previous work) to Ph: 2.79 ?2). Methylation and phenylation reactions of various prochiral aldehydes employing these methyllithium and phenyllithium aggregates yield alcohols with up to 44% ee. To rationalize the formation of the mixed (carb-)anionic aggregates, aggregate formation energies, describing co-condensations of RLi (R = Me, Ph, n-Bu) and lithium fencholates, are computed for the 3:1 and 2:2 stoichiometries. These computed aggregate formation energies point to preferences for 3:1 over 2:2 aggregates, as it is also apparent from experimental aggregate formations, confirmed by X-ray crystal analyses. In close analogy to the X-ray crystal structures, the computed Li3 surfaces increase with increasing steric demand of the carbanions. The chiral, mixed (carb-)anionic RLi-fencholate aggregates hence adapt to different carbanion sized and arise not only with small (Me) or primary carbanions (n-Bu) but even with the larger secondary phenyl anion.

Development of Chiral C2-Symmetric N-Heterocyclic Carbene Rh(I) Catalysts through Control of Their Steric Properties

Chiral square-planar Rh(I) complexes based on new C2-symmetric NHC ligands have been synthesized selectively in a few steps as single diastereoisomers. These chiral precatalysts were applied to the asymmetric transfer hydrogenation of 1-phenylp

Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis

Asymmetric hydrophosphination is the most atomically economical and straightforward approach to the construction of chiral organophosphorus compounds. Good stereoselectivities have been achieved in asymmetric hydrophosphination of an electron-deficient C=