936-91-4Relevant articles and documents
Synthesis of new enantiopure trans-3,4-diaminocaranes from (+)-3-carene
Cimarelli, Cristina,Fratoni, Davide,Palmieri, Gianni
, p. 603 - 608 (2011)
A synthetic strategy to obtain new enantiopure trans-3,4-diaminocaranes derived from (+)-3-carene via a stereoselective methodology is described. The stereoselective preparation of 3,4-α-carene- or 3,4-β-carene-epoxide is followed by a ring opening by sodium azide to obtain the azido-alcohols. Subsequent cyclization affords the corresponding aziridine diastereoisomers, which are converted to azido amines by opening of the aziridine rings by sodium azide and then reduced to the final diamine diastereoisomers. The absolute configurations of the final diamines and of novel intermediates are established by 1H NMR spectra correlated with conformational analysis supported by molecular modeling.
Synthesis of Aminoalkylated Aziridines from (+)-3-Carene
Curlat,Barba,Boldescu,Panekok,Macaev
, p. 269 - 274 (2019)
Aminoalkylated carane-type aziridines were synthesized via epoxidation of (+)-3-carene by H2O2 solution (7%) in EtOAc catalyzed by α-Al2O3 nanoparticles, opening of the epoxide by NaN3, and cyclization of the azidoalcohol by Ph3P followed by condensation of the resulting aziridines with formalin and secondary amines. The cytotoxicity of the aminoalkylated aziridines with heteroorganic substituents increased on going from a five-membered pyrrolidine ring substituent to a six-membered piperidine ring and decreased sharply upon replacing a piperidine by a morpholine ring or increased on going to a piperazine ring. The structures of products were established using IR and NMR spectroscopy and an X-ray crystal structure analysis.
Sustainable catalytic epoxidation of biorenewable terpene feedstocks using H2O2as an oxidant in flow microreactors
Bull, Steven D.,Cunningham, William B.,Plucinski, Pawel,Tibbetts, Joshua D.,Vezzoli, Massimiliano
supporting information, p. 5449 - 5455 (2021/08/16)
Solvent-free continuous flow epoxidation of the alkene bonds of a range of biorenewable terpene substrates have been carried out using a recyclable tungsten-based polyoxometalate phase transfer catalyst and aqueous H2O2 as a benign oxidant. These sustainable flow epoxidation reactions are carried out in commercial microreactors containing static mixing channels that enable common monoterpenes (e.g. untreated crude sulfate turpentine, limonene, etc.) to be safely epoxidized in short reaction times and in good yields. These flow procedures are applicable for the flow epoxidation of trisubstituted and disubstituted alkenes for the safe production of multigram quantities of a wide range of epoxides. This journal is
Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone
Banina,Sudarikov,Nigmatov,Frolova,Slepukhin,Zlotin,Kutchin
, p. 293 - 296 (2017/07/11)
Carane-derived β-amino alcohols with amino and hydroxy groups at positions 3 and 4 differing in their mutual arrangement and configuration were synthesized. Their application as organocatalysts in the asymmetric aldol reaction of isatin with acetone allowed one to obtain adducts with up to 84% enantiomeric excess.
