679431-93-7

Upstream product

• 1313885-27-6 C₁₄H₂₃ClO₂ 
• 187404-46-2 (R)-2-[1-phenyl-(E)-methylidene]-1-cyclohexyl acetate 
• 5682-83-7 (E)-2-benzylidenecyclohexanone 
• 108-94-1 cyclohexanone 
• 1400924-38-0 (R,E)-((2-(4-methylpentyl)cyclohexylidene)methyl)benzene 
• 77857-35-3 Cyclohexylidene-((S)-1-methoxymethyl-2-phenyl-ethyl)-amine 
• 903895-15-8 (S)-1-iodo-6-(4-methylpentyl)cyclohexene 

Relevant academic research and scientific papers

Enantioselective Protonation of Enol Esters with Bifunctional Phosphonium/Thiourea Catalysts

Bifunctional phosphonium/thioureas derived from tert-leucine behaved as highly selective catalysts for enantioselective protonation of enol esters, providing α-chiral ketones in yields of up to 99% with high enantioselectivities (up to 98.5:1.5 er). Control experiments clarified that a bulky tert-butyl group and phosphonium and thiourea moieties were necessary to achieve such high stereoselectivity. In addition, mechanistic investigations indicated the catalyst was converted to the corresponding betaine species, which served as a monomolecular catalyst.

Enantioselective route to ketones and lactones from exocyclic allylic alcohols via metal and enzyme catalysis

A general and efficient route for the synthesis of enantiomerically pure α-substituted ketones and the corresponding lactones has been developed. Ruthenium- and enzyme-catalyzed dynamic kinetic resolution (DKR) with a subsequent Cu-catalyzed α-allylic substitution are the key steps of the route. The α-substituted ketones were obtained in high yields and with excellent enantiomeric excess. The methodology was applied to the synthesis of a naturally occurring caprolactone, (R)-10-methyl-6-undecanolide, via a subsequent Baeyer-Villiger oxidation.

Copper-catalyzed preparation of ketones bearing a stereogenic center in α position

A highly enantioselective synthesis of α-alkylated and -arylated ketones can be achieved by using a reaction sequence consisting of a stereoselective anti-SN2′ allylic substitution in the presence of CuCN·2LiCl following by the oxidation of an intermediate cycloalkenyl lithium species using (Me3SiO)2 or (MeO) 3B/NaBO3·4H2O. (Chemical Equation Presented).

Novel Caprolactones from a Marine Streptomycete

Two new caprolactones, (R)-10-methyl-6-undecanolide (1) and (6R,10S)-10-methyl-6-dodecanolide (2), were identified in the lipid extract of a marine streptomycete (isolate B6007). Their structures were proposed on the basis of GC-MS experiments and proved by synthesis. The absolute configuration of the compounds was established by comparison of the natural and synthetic stereoisomers using chiral gas chromatography. These caprolactones show a moderate phytotoxicity and a promising activity against cancer cells with concomitant low general cytotoxicity.