107796-85-0

Upstream product

• 107733-24-4 3-naphthalen-1-yl-3H-isobenzofuran-1-one 
• 143490-16-8 (2R,4R)-2-(2-bromophenyl)-3-methyl-4-phenyl-1,3-oxazolidine 
• 143490-17-9 1,3-dihydro-1-hydroxy-3-(1-naphthyl)isobenzofuran 
• 107733-25-5 3-(6,7-dimethyl-1-naphthyl)-3-methylphthalide 
• 66-77-3 1-naphthaldehyde 
• 143490-19-1 (2S,4S)-2-(2-bromophenyl)-4-isopropyl-3-methyl-1,3-oxazolidine 
• 13922-41-3 1-Naphthylboronic acid 
• 4122-56-9 methyl o-formylbenzoate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 143490-20-4 (2S,4S)-2-(2-bromophenyl)-3,4-diisopropyl-1,3-oxazolidine 
• 88-65-3 2-bromobenzoic-acid 
• 5018-87-1 2-(naphthalene-1-carbonyl)-benzoic acid 
• 143490-18-0 (2R,4R)-2-(2-bromophenyl)-3-isopropyl-4-phenyl-1,3-oxazolidine 

Relevant academic research and scientific papers

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.

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%).

A new asymmetric synthesis of (R)- and (S)-3-arylphthalides: Extremely high diastereoselective reaction of arylcarbaldehydes with chiral [2-(1,3-oxazolidin-2-yl)phenyl]titanium ate complexes

Chiral [2-(1,3-oxazolidin-2-yl)phenyl]titanium ate complexes are prepared from the corresponding lithium complexes, and the extremely high diastereoselective reaction of arylcarbaldehydes with the chiral titanium ate complexes is performed. Then, optically pure (R)- and (S)-3-arylphthalides are synthesized in favorable yields and the chiral auxiliary reagents are recovered with no less of the optical purity.

Synthesis and Separation of Diastereomeric Imino Alcohol Derivatives of Chiral Phthalides: A Method for Assignment of Phthalide Absolute Configurations

Representative members of a series of chiral type 1 phthalides were converted with Lawesson's reagent to the corresponding thionophthalides.On treatment with any of several configurationally known chiral amino alcohols in the presence of mercuric trifluoroacetate, diastereomeric imino alcohols are afforded.These prove to be readily separable by chromatography on either silica or chiral stationary phases derived from the N-3,5-dinitrobenzamides of (R)-phenylglycine or (S)-leucine.Both the elution order of these diastereomers from silica and their 1H NMR chemical shift differences may be related to relative/absolute configurations.Hydrolysis of the separated imino alcohol diastereomers affords configurationally established phthalide enantiomers.On the basis of their CD spectra, it is concluded that the enantiomers of the entire series of phthalides elute from the chiral stationary phases in a uniform order