A one pot synthesis of various pyrrolidines via a tandem Michael addition-transition metal-catalysed cyclisation reaction

Tetrahedron Letters

Volumn 40, Issue 7, 1999, Pages 1301-1304

  Clique, Blandine ^a   Monteiro, Nuno ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

3 methylene pyrrolidines; Copper catalysed cyclisation; Michael addition; Propargyl amines

Indexed keywords

METAL DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0033547929     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02631-8     Document Type: Article

References (20)

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11. For an example of a related reaction, see: Sha, C-K; Tsou, C-P J. Org. Chem. 1990, 55, 2446-2450.
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18. Cis- addition of a zinc or a titanium enolate across unsaturated olefins or alkynes was recently reported: Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442-2450. Kitagawa, O.; Suzuki, T.; Inoue, T.; Taguchi, T. Tetrahedron Lett. 1998, 39, 7357-7360.
19. Cis- addition of a zinc or a titanium enolate across unsaturated olefins or alkynes was recently reported: Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442-2450. Kitagawa, O.; Suzuki, T.; Inoue, T.; Taguchi, T. Tetrahedron Lett. 1998, 39, 7357-7360.
20. While irradiation of the vinylic hydrogen resonance caused enhancement for the adjacent methyl protons and methylene protons α to the double bond, irradiation of the signal for vinylic methyl group resulted in significant enhancement of only the adjacent vinylic proton.