27877-66-3

Upstream product

• 67-56-1 methanol 
• 195250-21-6 4-(but-3-en-1-yloxy)-1,2-dimethoxybenzene 
• 1134201-61-8 C₁₂H₁₆O₃ 
• 2033-89-8 3,4-dimethoxyphenol 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 144465-19-0 (E)-3-(3,4-Dimethoxy-phenyl)-but-2-enoic acid methyl ester 
• 222312-35-8 3-(3,4-dimethoxy-phenyl)-butyric acid methyl ester 

Downstream Products

• 181222-28-6 4-(3-azido-1-methylpropyl)-1,2-dimethoxybenzene 

Relevant academic research and scientific papers

Helical triskelion monophosphites as ligands in asymmetric catalysis

Members of a new family of chiral triskelion P ligands, namely helical C3-symmetric monophos- phites P(OR)3, have been prepared in two steps Dy monoacylation of (R)- or (S)-1,1'-binaphthyl-2,2'-diol (BINOL) or diphenol using a carboxylic acid chloride followed Dy PCl3 phosphorylation. The most sterically hindered member of these monophosphites, derived from the compound accessible by monoacylation of BINOL using adamantane carboxylic acid chloride, has been characterized by X-ray crystallography and NMR spectroscopy as a single well-defined compound. It exists exclusively in the syn conformation, with a propeller-like (twisted) geometry resulting in helicity. Upon utilization of(R)- or (S)-BINOL in the two-step synthesis, the helicity proves to be P or M, respectively. When used as ligands in the Rh-catalyzed asymmetri c hydrogenation of prochiral homoallylic alcohols, these bulky helical ligands lead to respectable enantioselectivities (79-98percent ee). In contrast, the less sterically congested and more flexible BINOL-derived phenyl analogue exists in several conformeric forms, even in the crystal, and this leads to poor enantioselectivity in the model reactions (ee = 32percent). For the purpose of structural comparison, the analogous monophosphites derived from diphenol were also prepared and characterized. These compounds, again in contrast to the BINOL-derived adamantyl derivatives, occur in several different conformeric states.

Hypervalent iodine(III)-induced intramolecular cyclization reaction of substituted phenol ethers with an alkyl azido side-chain: A novel and efficient synthesis of quinone imine derivatives

Novel and efficient syntheses of quinone imine ketals (2aj) and quinone imines (4ah) from substituted phenol ethers (1ak) bearing an alkyl azido side-chain using the combination of hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA) and trimethylsilyl trifluoromethanesulfonate (TMSOTf), have been developed.

Intramolecular Photochemical Reactions of Bichromophoric 3-(Alkenyloxy)phenols and 1-(Alkenyloxy)-3-(alkyloxy)benzene Derivatives. Acid-Catalyzed Transformations of the Primary Cycloadducts

Irradiation of 3-(alkenyloxy)phenols and 1-(alkenyloxy)-3-(alkyloxy)benzene derivatives, at λ = 254 nm in acidic media, yields benzocyclobutenes, 3-alkylphenols, 3-alkylanisols, and 4-alkyl-1,2dialkyloxybenzenes depending on the substitution pattern of the aromatic ring and the olefinic side chain. The final products are derived from an intramolecular [2 + 2] photocycloaddition and acidic rearrangements from a common intermediate.