29941-87-5

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 765-87-7 cyclohexane-1,2-dione 
• 33832-15-4 5a,10a-dihydroxy-4a,9a-epoxyperhydrodibenzo<1,4>dioxine 
• 94532-19-1 2-isobutoxycyclohex-2-en-1-ol 

Downstream Products

• 94532-19-1 2-isobutoxycyclohex-2-en-1-ol 
• 116608-39-0 2-isobutoxy-1-methylcyclohex-2-en-1-ol 
• 92016-16-5 2-Hydroxy-cyclohexanon-⁽¹⁾-essigsaeure-⁽²⁾-aethylester 
• 94054-76-9 2-(2-Hydroxy-3-oxo-cyclohexylmethyl)-benzoic acid methyl ester 
• 81071-57-0 2-cyclopropyl-2-cyclohexen-1-one 
• 81071-59-2 2-cyclopropyl-2-hydroxycyclohexanone 
• 1438-96-6 (2-oxocyclohexyl)acetic acid 
• 90534-64-8 methyl 2-(6-oxocyclohex-1-en-1-yl)acetate 
• 75032-20-1 (1-Hydroxy-2-oxocyclohexyl)essigsaeure-methylester 
• 90200-01-4 2-(1-hydroxy-2-oxocyclohexyl)acetic acid 
• 1207204-54-3 2-isobutoxy-1-isopropylcyclohex-2-enol 
• 94531-93-8 2-bromo-1-ethoxy-1-(2-isobutoxy-1-methylcyclohex-2-enyloxy)ethane 
• 94532-17-9 2-bromo-1-ethoxy-1-(2-isobutoxycyclohex-2-enyloxy)ethane 

Relevant academic research and scientific papers

The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: Reaction development, scope, and applications

The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (-)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbonate and tert-butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of chloroform as solvent allows the use of ambient air as the terminal oxidant at 23°C, resulting in enhanced catalyst selectivity. These improved reaction conditions have permitted the successful kinetic resolution of benzylic, allylic, and cyclopropyl secondary alcohols to high enantiomeric excess with good-toexcellent selectivity factors. This catalyst system has also been applied to the desymmetrization of meso-diols, providing high yields of enantioenriched hydroxyketones.

Palladium-catalyzed enantioselective oxidation of chiral secondary alcohols: Access to both enantiomeric series

(Chemical Equation Presented) Rapid resolution: A new catalyst system for the oxidative kinetic resolution of secondary alcohols leads to dramatic rate increases. This system allows the use of a diamine to provide access to either enantiomer of a range of alcohols with good selectivity factors (see scheme). This method has been applied to the formal total synthesis of (-)-amurensinine.

Thermal Rearrangements of 2-Cyclopropylcycloalk-2-enones

Thermolysis of 2-(2,2-dimethylcyclopropyl)cyclopent-2-enone (2) and 2-cyclopropylcyclohex-2-enone (6) is shown to produce 2-(3-methylbut-2-enylidene)cyclopentanone (10) and 2-propylphenol (14), respectively, via homosigmatropic H-migration and isomerisation.Heating 2-cyclopropylcyclopent-2-enone (8) under a variety of conditions led only to decomposition; no products resulting from vinylcyclopropane - cyclopentene rearrangement were detected.