76519-87-4

Upstream product

• 628-92-2 Cycloheptene 

Downstream Products

• 1056246-49-1 2-bromocycloheptanone 
• 932-57-0 (+/-)-trans-2-aminocycloheptanol 
• 502-41-0 cycloheptanol 
• 100199-26-6 (1S,2S)-1-(4-Fluoro-phenyl)-2-imidazol-1-yl-cycloheptanol 
• 100199-30-2 (1S,2S)-1-(4-Chloro-phenyl)-2-imidazol-1-yl-cycloheptanol 
• 1643952-46-8 8-(2,4-dinitrobenzoyl)-8-azabicyclo[5.1.0]octane 
• 1643952-56-0 C₂₁H₂₁N₃O₇ 
• 13553-19-0 cis-Cycloheptan-1,2-diol 
• 110162-59-9 cis-8,10-Dioxabicyclo<5.3.0>decan-9-one 
• 108268-28-6 (1R,2R)-cycloheptane-1,2-diol 
• 13553-19-0 (1S,2S)-cycloheptane-1,2-diol 
• 13553-19-0 trans-cycloheptane-1,2-diol 

Relevant academic research and scientific papers

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).

Activation of carboxylic acids in asymmetric organocatalysis

Organocatalysis, catalysis using small organic molecules, has recently evolved into a general approach for asymmetric synthesis, complementing both metal catalysis and biocatalysis.1 Its success relies to a large extent upon the introduction of novel and generic activation modes.2 Remarkably though, while carboxylic acids have been used as catalyst directing groups in supramolecular transition-metal catalysis,3 a general and well-defined activation mode for this useful and abundant substance class is still lacking. Herein we propose the heterodimeric association of carboxylic acids with chiral phosphoric acid catalysts as a new activation principle for organocatalysis. This self-assembly increases both the acidity of the phosphoric acid catalyst and the reactivity of the carboxylic acid. To illustrate this principle, we apply our concept in a general and highly enantioselective catalytic aziridine-opening reaction with carboxylic acids as nucleophiles. Activation by dimerization: There is still no general activation mode for carboxylic acids in organocatalysis. The formation of heterodimers between chiral phosphoric acid diesters and carboxylic acids can be used to activate and direct reactivity of the latter in asymmetric reactions. This novel principle has been applied to the ring-opening desymmetrization and kinetic resolution of aziridines leading to valuable amino alcohols.