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Université Paris Sud, Equipe de Chimie des Substances naturelles, UMR CNRS 8076 BioCIS, 5, rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry Cedex, France
; Fax: +33 (0)146835250
; Tel: +33 (0)146835730
Université Paris Sud, Service commun d'analyses, UMR CNRS 8076 BioCIS, 5, rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry Cedex, France
; Fax: +33 (0)146835828
; Tel: +33 (0)146835652
Institut de Chimie des Substances Naturelles, UPR CNRS 2301, Bâtiment 27, 1, Avenue de la Terrasse, F-91198 Gif-sur-Yvette cedex, France
; Tel: +33 (0)169824583
Org. Biomol. Chem., 2012,10, 7148-7157
18 May 2012,
03 Jul 2012
First published online
04 Jul 2012
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.