26771-11-9Relevant articles and documents
Novel Enantioselective Syntheses of Optically Active (1R)-cis- and (1R)-trans-Chrysanthemic Acids.
Krief, Alain,Surleraux, Dominique,Ropson, Nathalie
, p. 289 - 292 (1993)
Dimethyl dimedone, a non chiral and cheap compound, has been converted to the optically actives 1-(R)-cis- and 1-(R)-trans-chrysanthemic acids possessing high economic value.These processes involve as the key steps (i) a cyclopropanation reaction (ii) a Grob fragmentation and (iii) a lipase monitored hydrolysis of a prochiral diacetate.
Cyclopropanation of Terminal Alkenes through Sequential Atom-Transfer Radical Addition/1,3-Elimination
Tappin, Nicholas D. C.,Michalska, Weronika,Rohrbach, Simon,Renaud, Philippe
supporting information, p. 14240 - 14244 (2019/08/26)
An operationally simple method to affect an atom-transfer radical addition of commercially available ICH2Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one-pot process into the corresponding cyclopropane upon treatment with a fluoride source. This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non-terminal alkenes and electron-deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated.
Syntheses of racemic and scalemic cis-chrysanthemic acid from β,γ-unsaturated cyclohexanol
Krief, Alain,Jeanmart, Stéphane,Gondal, Humaira Y.,Kremer, Adrian
, p. 2123 - 2167 (2013/02/23)
2,2,5,5-Tetramethylcyclohexane-1,3-dione is a valuable starting-material precursor of cis-chrysanthemic acid. The (1S)-stereoisomer is a precursor of pyrethrin I, the most active natural insecticide from Chrysanthemum cinerariifolium, whereas the (1R)-stereoisomer is efficiently transformed to deltamethrin, the most active commercially available pyrethroid insecticide. Several intermediates have been identified and used with variable success for that purpose.