Synthesis of trans-4,5-diaminocyclopent-2-enones from furfural catalyzed by Er(III) immobilized on silica

A New Approach to the Synthesis of Functionalized Bicyclo[3.2.1]octanes

“…We suppose that the intermediate 2 further undergoes spontaneous Nazarov-type 4π-electrocyclization [17] to give 2,3diaminocyclopentenones 3. The formation of 3 from furfural and amines is well known and described in recent literature (e.g., [18][19][20][21][22][23][24][25], see also the review by Piancatelli et al [26]). When furfural and isopropyl cyanoacetate were added to the reaction mixture, 3-(2-furyl)-2-cyanoacrylate 4 and Michael adduct 5 were formed sequentially.…”

Synthesis and Applications of Stenhouse Salts and Derivatives

“…[14] Later on, Afonso et al reported the use of erbium(III) immobilized on silica as ar eusable catalyst. [15] In 2017, am ethod to prepare CP in water under microwave irradiation (60 8C, 5min) was described by Nardi and co-workers. [16] Ac oncise description of these methodologies can be found in Ta ble 1.…”

A designed and potentially decadentate ligand for use in lanthanide(iii) catalysed biomass transformations: targeting diastereoselectivetrans-4,5-diaminocyclopentenone derivatives

“…Batey and coworkers was first reported the utilisation of Dy(OTf ) 3 as Lewis acid to catalyse a domino condensation/ring-opening/electrocyclization process. 6 This pioneer study led to an increasing number of alternative strategies for the formation of trans-4,5-diamino-cyclopent-2-enone derivatives such as the employment of the ionic liquid 1-methylimidazolium tetrafluoroborate, 16 tosylamine metal free catalyst, 17 Al(Cl) 3 , 18 3d/4fclusters, 19,20 ErCl 3 10 or ErCl 3 immobilized on silica, 21 under microwave irradiation 22 and Cu(OTf ) 2 in water as a reusable catalyst. 23 A recent report from Batey and co-workers revealed the efficiency of the Dy(OTf ) 3 catalyst for the transformation of the substituted furfuraldehydes to 3-substituted-trans-4,5cyclopentenone in high stereoselectively and yield.…”