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Upstream product

• 87443-43-4 [2-((4S,5S)-4-Methoxymethyl-5-phenyl-4,5-dihydro-oxazol-2-yl)-phenyl]-phenyl-methanone 
• 85-52-9 2-Benzoylbenzoic acid 
• 606-28-0 methyl o-benzoylbenzoate 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 100-52-7 benzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 93-89-0 benzoic acid ethyl ester 
• 77250-60-3 (4S,5S)-2-(2-bromophenyl)-4-methoxymethyl-5-phenyl-2-oxazine 
• 1055981-44-6 (S)-2-benzoyl-N-(α-phenylethyl)benzamide 
• 87-41-2 2-benzofuran-1(3H)-one 
• 65184-67-0 1,3-dihydro-1-hydroxy-3-phenylisobenzofuran 
• 5398-11-8 3-phenylphthalide 
• 604-61-5 ethyl 2-benzoylbenzoate 
• 16780-82-8 2-benzoylbenzaldehyde 

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.

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

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.

Rhodium(III)-Catalyzed Asymmetric Addition of Inert Arene C-H Bond to Aldehydes to Afford Enantioenriched Phthalides

An asymmetric rhodium(III)-catalyzed Grignard-type addition of inert arene C-H bond to aldehydes is reported. It provides a new strategy for the synthesis of chiral 3-substituted phthalides in good yields (up to 87%) with high enantiomeric purity (up to 99% ee). Interestingly, a chiral-matching effect between substrate and catalyst was observed, which is crucial to accomplish satisfied reaction outcomes. Mechanistically, the reaction is assumed to proceed via consecutive C(sp2)-H activation of benzamide, addition to aldehyde, and lactonization.

Highly Enantioselective Cobalt-Catalyzed Hydroboration of Diaryl Ketones

A highly enantioselective cobalt-catalyzed hydroboration of diaryl ketones with pinacolborane was developed using chiral imidazole iminopyridine as a ligand to access chiral benzhydrols in good to excellent yields and ee. This protocol could be carried out in a gram scale under mild reaction conditions with good functional group tolerance. Chiral biologically active 3-substituted phthalide and (S)-neobenodine could be easily constructed through asymmetric hydroboration as a key 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.

Lewis acid-assisted dirhodium(II)-catalyzed ketone hydroacylation

The combination of a Rh(II) salt and a Lewisacid, Sc(OTf)3, as a highly active and robust cooperative catalyst system for ketone hydroacylation was developed. The catalyst system showed high turnover numbers (up to ca. 400) even under air, whereas the corresponding Rh(I)/Sc(OTf)3 system did not work well. The application of the Rh(II)/Sc system was also extended to hydroacylation of olefins and an enantioselective reaction.

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.

Enantioselective addition of arylboronic acids to methyl 2-formylbenzoates by using a ruthenium/Me-BIPAM catalyst for synthesis of chiral 3-aryl-isobenzofuranones

Ruthenium/Me-BIPAM-catalyzed asymmetric addition of arylboronic acids to methyl 2-formylbenzoates afforded chiral 3-aryl-isobenzofuranones. [RuCl2(p-cymene)]2/Me-BIPAM and RuCl2(PPh3)3/Me-BIPAM catalyst systems tolerate a variety of functional groups and give high yields with high enantioselectivities.