72407-62-6

Upstream product

• 23283-97-8 (+)-(1S,2R,5R)-isomenthol 
• 2216-51-5 (-)-menthol 
• 2243-83-6 2-naphthaloyl chloride 
• 15356-70-4 menthol 
• 490-99-3 DL-neomenthol 
• 76373-11-0 1-bromo-2-naphthoyl chloride 
• 20717-79-7 1-bromo-2-naphthoic acid 
• 76373-12-1 l-menthyl 1-bromo-2-naphthoate 

Downstream Products

• 1186614-32-3 C₄₂H₅₂O₄ 
• 1186614-34-5 C₄₂H₅₂O₄ 
• 1186614-33-4 C₄₂H₅₂O₄ 

Relevant academic research and scientific papers

Diastereoselective photocycloaddition reactions of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furans governed by chiral auxiliaries and hydrogen bonding interactions

By using chiral auxiliaries and hydrogen bonding interactions, we have developed diastereoselective photocycloaddition of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furan derivatives. In photoreactions of (?)-menthyl 2-naphthalenecarboxylate with furan and 3-furanmethanol, respective maximum 48% and 40% diastereomeric excesses (d.e.) are observed. In photoreactions of di-8-phenyl-(?)-menthyl 2,3-naphthalenedicarboxylate with 3-furanmethanol, maximum 67% d.e. is obtained. Use of solvents of low polarity, low temperatures and low furan concentration leads to increased diastereoselectivities. Variable-temperature (VT) NMR and fluorescence quenching studies indicate that hydrogen bonding interactions between the carbonyl oxygen of naphthalenecarboxylic acid esters and the OH group in 3-furanmethanol take place in both the ground and excited states. The results of computational studies show that geometries of C2 symmetric naphthalenedicarboxylate reactants are important in governing the high diastereoselectivity in the photoreactions of 2,3-naphthalenedicarboxylates.

Diastereodifferentiating photodimerization of alkyl 2-naphthoates with chiral auxiliaries

Photodimerization of alkyl 2-naphthoates with chiral auxiliaries resulted in cubane-like anti head-to-head photodimers in 93% yield and with up to 59% diastereomeric excess. After removal of the chiral auxiliaries enantiomers of cubane-like photodimer of 2-naphthalene carboxylic acid were obtained in 80% yield.

Enantiodifferentiating Cis-Trans Photoisomerizations of 1,2-Diarylcyclopropanes and 2,3-Diphenyloxirane Sensitized by Chiral Aromatic Esters

Photosensitized enantiodifferentiating cis-trans isomerizations of 1,2-diphenylcyclopropane (1), 1,2-bis(4-methoxyphenyl)cyclopropane (2), and 2,3-diphenyloxirane (3) were performed in the presence of optically active alkyl arenecarboxylates as electron-accepting photosensitizers.Several photosensitizers possessing different chromophores and chiral groups were examined in polar and nonpolar solvents, and optical purities (op) up to 10percent for 1t and 1percent for 2t and 3t were obtained.The product's op varied drastically with solvent polarity and, in an extreme case, typical polar and nonpolar solvents gave antipodal products.Mechanistic investigations revealed that the enantiodifferentiation occurs in the quenching of the excited chiral sensitizer by racemic substrates and that full equilibrium is not established between the enantiomeric ambident intermediates, probably owing to their short lifetimes.

PARTIAL ASYMMETRIC SYNTHESIS OF ATROPISOMERIC 1,1'-BINAPHTHYLS VIA THE ULLMANN COUPLING REACTION OF CHIRAL ALCOHOL ESTERS OF 1-BROMO-2-NAPHTHOIC ACID

The Ullmann coupling of 1-bromo-2-naphthoates of C-chiral alcohols of R- and S-configuration induced axial dissymmetry of R- and S-chirality, respctively, in the newly formed 1,1'-bond of the binaphthyls; the optical yield amounted up to 13percent where the chiral alcohol was l-menthol.