874672-43-2

Upstream product

• 1055981-47-9 (S)-2-(4'-methoxybenzoyl)-N-(α-phenylethyl)benzamide 
• 4122-56-9 methyl o-formylbenzoate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1160755-76-9 p-anisylmethylzinc 
• 23864-91-7 2-(4-methoxybenzoyl)benzaldehyde 
• 52898-49-4 4,N-dimethoxy-N-methylbenzamide 
• 35822-58-3 2-bromobenzaldehyde diethyl acetal 
• 1017266-40-8 C₉H₁₂OZn 
• 6940-49-4 3-Bromophthalide 
• 118-90-1 ortho-methylbenzoic acid 
• 87-41-2 2-benzofuran-1(3H)-one 
• 1151-15-1 2-(4-methoxybenzoyl)benzoic acid 
• 85-44-9 phthalic anhydride 

Relevant academic research and scientific papers

Enantioselective synthesis of 3-aryl-phthalides through a nickel-catalyzed stereoconvergent cross-coupling reaction

A nickel-catalyzed asymmetric Suzuki-Miyaura cross-coupling of racemic 3-bromo-phthalides and arylboronic acids was realized for the synthesis of diverse chiral 3-aryl-phthalides in moderate to excellent reaction yields. The reaction proceeded in a stereoconvergent manner and high enantioselectivities were observed for most examined examples. A number of functional groups like aldehyde, ester and bromide were well tolerated. Heteroaromatic boronic acids were also competent coupling partners in this reaction.

Cationic Iridium/Chiral Bisphosphine-Catalyzed Enantioselective Hydroacylation of Ketones

A facile and convenient synthesis of the chiral phthalide framework catalyzed by cationic iridium was developed. The method utilized cationic iridium/bisphosphine-catalyzed asymmetric intramolecular carbonyl hydroacylation of 2-keto benzaldehydes to furnish the corresponding optically active phthalide products in good to excellent enantioselectivities (up to 98% ee). The mechanistic studies using a deuterium-labelled substrate suggested that the reaction involved an intramolecular carbonyl insertion mechanism to iridium hydride intermediate. In addition, we investigated the kinetic isotope effect (KIE) of intramolecular hydroacylation with deuterated substrate and determined that the C?H activation step is not included in the turnover-limiting step.

Catalytic asymmetric 1,2-Addition/Lactonization tandem reactions for the syntheses of chiral 3-Substituted phthalides using organozinc reagents

Using chiral phosphoramide ligand 2d-Zn (II) complex derived from (1R,2R)-1,2-diphenylethylenediamine as the catalyst, we have developed efficient catalytic asymmetric 1,2-addition/lactonization tandem reactions of diverse organozinc reagents with varied methyl 2-formylbenzoates for the construction of optically enriched 3-aryl or alkyl substituted phthalides, which are significant building blocks of many important chiral pharmaceuticals and natural products. The corresponding products could be afforded with good to excellent yields (up to 95%) and moderate to good enantioselectivities (up to 89%).

Catalytic asymmetric synthesis of 3-aryl phthalides enabled by arylation-lactonization of 2-formylbenzoates

The catalytic asymmetric synthesis of 3-aryl phthalides is reported through a sequential asymmetric arylation-lactonization reaction. The reaction is enabled by a boron-zinc exchange to generate reactive arylating agents, which react with 2-formylbenzoates in the presence of a chiral amino naphthol ligand. The enantiodetermining step is the arylation of the aldehyde, which then undergoes a lactonization event to yield the corresponding phthalides in good yields and enantioselectivities.

Ruthenium-Catalyzed Enantioselective Hydrogenation/Lactonization of 2-Acylarylcarboxylates: Direct Access to Chiral 3-Substituted Phthalides

Highly enantioselective tandem hydrogenation/lactonization of various 2-acylarylcarboxylates including 2-aroylarylcarboxylates were realized by using [RuCl(benzene)(S)-SunPhos]Cl as the catalyst under mild reaction conditions. Excellent enantioselectivities (up to 99.6 % ee) and activities (S/C=1000) were obtained. This convenient and practical method enables a direct access to a series of highly optically pure 3-substituted phthalides that are very important molecules as valuable pharmacological compounds and diversified synthons for medicinal chemistry. Moreover, a gram-scale reaction was performed to further demonstrate the practicality of this approach.

Diastereomeric aziridine carbinol catalyzed enantioselective arylation reaction: Toward the asymmetric synthesis of both enantiomers of chiral 3-aryl phthalide

The diastereomeric aziridine carbinols are applied, respectively, as efficient chiral ligand in the catalysis of asymmetric arylation and sequential arylation-lactonization cascade. The two diastereomers, which are facilely synthesized from the same chiral source, function as pseudo enantiomers in arylation of aromatic aldehydes providing the different enantiomers of the diarylmethanols with almost the same excellent enantioselectivities. The arylation method is also carried out in tandem with lactonization process to afford a concise synthetic approach to both enantiomers of optically active 3-aryl phthalide.

Cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and olefins

Cobalt-chiral diphoshine catalytic systems promote intramolecular hydroacylation reactions of 2-acylbenzaldehydes and 2-alkenylbenzaldehydes to afford phthalide and indanone derivatives, respectively, in moderate to good yields with high enantioselectivities. The ketone hydroacylation did not exhibit a significant H/D kinetic isotope effect (KIE) with respect to the aldehyde C-H bond, indicating that C-H activation would not be involved in the rate-limiting step.

Transition metal-catalyzed addition reactions of arylboronic acids with alkyl 2-formylbenzoates: Efficient access to chiral 3-substituted phthalides

Transition metal-catalyzed addition of arylboronic acids to 2-formylbenzoates afforded 3-substituted phthalides. By using SPINOL-based phosphites as ligands, a Rh(i)-catalyzed asymmetric version of such an addition reaction was achieved. The Royal Society of Chemistry 2010.

Cascade enantioselective synthesis of 3-arylphthalides using chiral auxiliary route

An enantioselective synthesis of 3-arylphthalides was achieved using (S)-1-phenylethylamine as a chiral auxiliary. Reduction of chiral keto amides of 2-aroylbenzoic acids followed by acid-catalyzed lactonization yielded (S)-3-arylphthalides with 75-85% ee.