32019-31-1

Upstream product

• 123-38-6 propionaldehyde 
• 28987-79-3 m-tolylmagnesium bromide 
• 10467-10-4 ethylmagnesium iodide 
• 620-23-5 m-tolyl aldehyde 
• 925-90-6 ethylmagnesium bromide 
• 74-96-4 ethyl bromide 
• 557-20-0 diethylzinc 
• 536-74-3 phenylacetylene 
• 591-17-3 meta-bromotoluene 
• 2386-64-3 ethylmagnesium chloride 
• 587-03-1 3-methylbenzyl alcohol 
• 51772-30-6 3'-Methylpropiophenone 

Downstream Products

• 51772-30-6 3'-Methylpropiophenone 
• 56004-97-8 1-(1-bromopropyl)-3-methylbenzene 
• 2077-32-9 1-methyl-3-[(1E)-prop-1-en-1-yl]benzene 

Relevant academic research and scientific papers

The application of chiral aminonaphthols in the enantioselective addition of diethylzinc to aryl aldehydes

(Equation presented) Optically active aminonaphthol 3 obtained by condensation of 2-naphthol, benzaldehyde, and (S)-methylbenzylamine followed by N-methylation was found to catalyze the enantioselective ethylation of aryl aldehydes to secondary alcohols w

Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds

The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.

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.

Binaphthyl-based chiral ligands: Design, synthesis and evaluation of their performance in enantioselective addition of diethylzinc to aromatic aldehydes

The design strategy and the performance of binaphthyl-based chiral ligands were evaluated with computation and enantioselective addition of diethylzinc to aromatic aldehydes. Under optimized conditions, enantioselective addition of diethylzinc to aromatic aldehydes provided the desired optically active secondary alcohols in high isolated yields (up to 91%) and excellent enantiomeric excesses (up to 98% ee).

Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Novel Thiophene-Based Chiral Ligands

Abstract: Chiral norephedrine-derived β-amino alcohols with a thiophene moiety were synthesized from thiophene carbaldehydes (methyl- or ethyl-substituted) and chiral amino alcohols, such as both enantiomers of norephedrine and 2-aminopropanol. The synthesized ligands were applied to the catalytic asymmetric addition of diethylzinc to aldehydes to obtain optically active alcohols with a high conversion (92%) and excellent enantioselectivities (ee up to 99%). The highest enantioselectivity (ee 99%) was obtained with p-trifluorobenzaldehyde as the substrate containing the strongly electron-acceptor CF3 group.

Synthetic method of 3 '-methyl propiophenone

The invention belongs to the field of organic synthesis, and discloses a synthetic method of 3 '-methyl propiophenone. The method comprises the following steps: taking m-tolualdehyde as a raw material, carrying out affinity addition reaction with an ethyl Grignard reagent to obtain 3 '-methyl phenylpropanol; and then using oxygen as an oxidizing agent, using a composite catalyst composed of nitroxide free radicals, inorganic bromide and nitrite, and performing catalytic oxidation on 3 '-methyl phenylpropanol to generate 3'-methyl propiophenone. The adopted composite catalyst is good in stability and selectivity, high in yield (up to 90% or above), reusable, safe and environment-friendly in the whole process and suitable for industrial production.

Chiral P,N-ligands for the highly enantioselective addition of diethylzinc to aromatic aldehydes

A new sterically hindered chiral P,N-ligand was synthesized and successfully applied to copper catalyzed asymmetric addition of diethylzinc to aromatic aldehydes. Various aromatic aldehydes can react smoothly to give the corresponding addition products with good to excellent enantioselectivities, which provides a readily accessible method for the preparation of chiral secondary alcohols.

Enantioselective addition of diethylzinc to aldehydes catalyzed by 5-cis-substituted proline derivatives

5-Cis-substituted prolinols, prolinamines, and prolinamine sulfonamides proved to be efficient ligands for the enantioselective addition of diethylzinc to aldehydes, providing up to 99% ee. The sense of asymmetric induction can be controlled by the nature

Chiral zinc amidate catalyzed additions of diethylzinc to aldehydes

A series of bifunctional spiro ligands bearing “carboxamide–phosphine oxide” groups and ethylzinc carboxamidates from these ligands as catalysts for Et2Zn additions to aldehydes were reported. Excellent yields were obtained with moderate ee′s in Et2Zn additions to benzaldehyde derivatives, implying effectiveness of our newly designed catalytic structures as well as mediocre stereocontrol by these chiral ligands. Possible transition states were suggested based on the crystal structures of two ligands.

New C2-symmetric six-membered carbene ligands for asymmetric diethylzinc addition of arylaldehydes

A series of new six-membered NHC precursors were prepared by simply esterification of their parent compounds. Their applicability in asymmetric diethylzinc addition of arylaldehydes has been demonstrated and the corresponding secondary alcohol was obtained with good yields and moderate enantioselectivities. (Figure pressented)