106561-14-2

Upstream product

• 100-52-7 benzaldehyde 
• 51276-70-1 diheptylmagnesium 
• 124-13-0 Octanal 
• 1078-58-6 diphenylzinc 
• 98-80-6 phenylboronic acid 
• 123824-37-3 (α-acetoxyoctyl)benzene 
• 1674-37-9 n-octanophenone 
• 629-06-1 1-Chloroheptane 
• 131320-88-2 (S)-(-)-1-phenyl-1-octanol acetate 

Relevant academic research and scientific papers

Catalytic asymmetric arylation of aliphatic aldehydes using a B/Zn exchange reaction

Herein we describe the arylation of aliphatic aldehydes using the boron/zinc exchange reaction for the generation of transferable aryl groups, in the presence of chiral amino alcohol ligands. For the first time, a systematic investigation of this reaction

Enantioselective arylation of aldehydes catalyzed by a soluble optically active polybinaphthols ligand

A soluble chiral polymer ligand was synthesized by the polymerization of (R)-6,6′-dibutyl-3,3′-diformyl-2,2′-binaphthol (R-M-1) with 2,5-diaminopyridine (M-2) via a nucleophilic addition-elimination reaction. While arylboronic acids were used as the source of the transferable aryl group, the chiral polybinaphthols ligand in combination with Et2Zn without Ti(OiPr)4 exhibited higher enantioselectivity in asymmetric addition to aromatic aldehydes than alphatic aldehydes. When aromatic aldehydes with electron-withdrawing groups were chosen as substrates, the resulting diarylmethanols were produced in higher ee values than those with electron-donating groups as substrates. 2-Naphthaldehyde used as a substrate afforded product in 95% ee, which could be ascribed to the steric effect influence on this asymmetric arylation reaction. Moreover, the chiral polymer was easily recovered and reused, but exhibited a decrease of enantioselectivity in the third recycle.

Enantioselective alkylation of aldehydes with chiral organomagnesium amides (COMAs)

(graph presented) Dialkylmagnesiums react with chiral secondary amines to form chiral organomagnesium amides (COMAs). These reagents alkylate aldehydes to form secondary alcohols with enantioselectivities up to 91:9 er.

A new chiral sulfinyl-NH-pyridine ligand for Ir-catalyzed asymmetric transfer hydrogenation reaction

A new flexible C1-symmetric tridentate ligand (S)-N-(2-(tert-butylsulfinyl)benzyl)-1-(pyridin-2-yl)methanamine sulfoxide (L1) was successfully prepared and utilized as a chiral ligand for Ir(I)-catalyzed ATH (asymmetric transfer hydrogenation) reactions. Without any cooperation of other chiral center, encouraging ee and conversion values have been achieved, which provide us a better understanding on these types of ligands and a new strategy to develop new high-efficiency chiral catalysts for asymmetric reaction.

PROCESS FOR PRODUCING OPTICALLY ACTIVE ALCOHOL

Disclosed is a method for producing an optically active alcohol including reacting a titanium compound, an aromatic magnesium compound and a carbonyl compound in the presence of an optically active biphenol compound having a predetermined structure and an ether compound having a predetermined structure.

A concise synthesis of (S)-(+)-ginnol based on catalytic enantioselective addition of commercially unavailable Di(n -alkyl)zinc to aldehydes and ketones

Catalytic, enantioselective n-alkyl addition of commercially unavailable di(n-alkyl)zinc reagents, which were prepared by a refined version of Charettes procedure with Grignard reagents, to aldehydes and ketones was developed. To minimize the side reactions in the catalysis by chiral phosphoramide ligand (1) or 3,3-diphosphoryl-BINOL ligand (2), a preparation of di(n-alkyl)zinc reagents with a 1:2.5:1.6 molar ratio of ZnClNaOMe/RMgCl under solvent-free conditions was essential. Optically pure (S)-(+)-ginnol (17) was readily synthesized in one step for the first time by the catalytic enantioselective n-nonylation of icosanal. Georg Thieme Verlag.

Emerging solvent-induced homochirality by the confinement of achiral molecules against a solid surface

One hand mapping: By means of scanning tunneling microscopy, solvent-induced homochirality is shown to emerge in self-assembled monolayers of achiral molecules at the liquid-solid interface (see picture). The chirality of the solvent directs the macroscopic chirality of the monolayer. The dynamics of the monolayer structure as it evolves towards homochirality are probed by time-dependent measurements. (Figure Presented)

Synthesis of the bifunctional BINOL ligands and their applications in the asymmetric additions to carbonyl compounds

Efficient one-step syntheses of the bifunctional BINOL and H8BINOL ligands (S)-6 and (S)-8 have been developed from the reaction of BINOL and H8BINOL with morpholinomethanol, respectively. The X-ray analyses of these compounds have revealed their structural similarity and difference. The bifunctional H8BINOL (S)-8 is found to be highly enantioselective for the reaction of diphenylzinc with many aliphatic and aromatic aldehydes and especially is the most enantioselective catalyst for linear aliphatic aldehydes. Unlike other catalysts developed for the diphenylzinc addition which often require the addition of a significant amount of diethylzinc with cooling (or heating) the reaction mixture in order to achieve high enantioselectivity, using (S)-8 needs no additive and gives excellent results at room temperature. (S)-8 in combination with diethylzinc and Ti(OiPr)4 can catalyze the highly enantioselective phenylacetylene addition to aromatic aldehydes. It can also promote the phenylacetylene addition to acetophenone at room temperature though the enantioselectivity is not very high yet. Without using Ti(OiPr)4 and a Lewis base additive, (S)-8 in combination with diethylzinc can catalyze the reaction of methyl propiolate with an aldehyde to form the highly functional γ-hydroxy-α,β-acetylenic esters except that the enantioselectivity is low at this stage. The bifunctional BINOL ligand (S)-6 in combination with Me2AlCl is found to be a highly enantioselective catalyst for the addition of TMSCN to both aromatic and aliphatic aldehydes.

Highly enantioselective addition of diphenylzinc to aliphatic and aromatic aldehydes catalyzed by a readily available H8-binol derivative

(Chemical Equation Presented) All sorts of aldehydes 2 (R = aryl, vinyl, branched, and linear alkyl) undergo the highly enantioselective addition of diphenylzinc (1) in the presence of catalytic (S)-4 to give α-substituted benzyl alcohols 3 in high yields. In contrast to previous catalysts, no additive is required, the reaction is carried out at room temperature, and the reaction is equally effective with linear aldehydes.

Enzymatic Preparation of the Enantiomers of Some 1-Phenyl-1-alkanols

The acetates of racemic 1-phenyl-1-heptanol, 1-phenyl-1-octanol and 1-phenyl-1-nonanol were hydrolyzed by Pseudomonas lipase in 10percent acetone-0.1 M phosphate buffer (pH 6.9) at 30 deg C.Due to remarkable differences in the rates of hydrolysis of the e