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Issue 35, 2012
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Solvent-free double aza-Michael under ultrasound irradiation: diastereoselective sequential one-pot synthesis of pyrrolidine Lobelia alkaloids analogues

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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.

Graphical abstract: Solvent-free double aza-Michael under ultrasound irradiation: diastereoselective sequential one-pot synthesis of pyrrolidine Lobelia alkaloids analogues

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Publication details

The article was received on 18 May 2012, accepted on 03 Jul 2012 and first published on 04 Jul 2012


Article type: Paper
DOI: 10.1039/C2OB25963J
Citation: Org. Biomol. Chem., 2012,10, 7148-7157
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    Solvent-free double aza-Michael under ultrasound irradiation: diastereoselective sequential one-pot synthesis of pyrrolidine Lobelia alkaloids analogues

    Z. Amara, E. Drège, C. Troufflard, P. Retailleau and D. Joseph, Org. Biomol. Chem., 2012, 10, 7148
    DOI: 10.1039/C2OB25963J

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