title: Solvent-free double aza-Michael under ultrasound irradiation: diastereoselective sequential one-pot synthesis of pyrrolidine Lobelia alkaloids analogues.
abstract: Novel 2,5-meso-pyrrolidines have been straightforwardly synthesized from readily available symmetrical double Michael acceptors. The key step rested on an aza-Michael addition of primary alkylamines to bis-enones. Competitive Rauhut-Currier and aza-Michael reactions have been highlighted in protic solvent. Ultrasound activation associated with solvent-free conditions led to the expected pyrrolidines in quantitative yields and excellent stereoselectivities. The optimized conditions have been extended to the sonochemical synthesis of pyrrolidine Lobelia alkaloids analogues in short sequences.
authors: Université Paris Sud, Equipe de Chimie des Substances naturelles, UMR CNRS 8076 BioCIS, Châtenay-Malabry, France.
authors: Zacharias
authors: Z
authors: Amara
authors: Emmanuelle
authors: E
authors: Drège
authors: Claire
authors: C
authors: Troufflard
authors: Pascal
authors: P
authors: Retailleau
authors: Delphine
authors: D
authors: Joseph
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D029746:Lobelia / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013016:Sound; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011759:Pyrrolidines