Solid-phase synthesis of pyrrolidines via 2-azaallyl anion cycloadditions with alkenes

Tetrahedron Letters

Volumn 38, Issue 44, 1997, Pages 7669-7672

  Pearson, William H ^a   Clark, Roger B ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; ELECTRON TRANSPORT; ORGANIC CHEMISTRY; POLYMERIZATION; REACTION ANALYSIS; SOLID PHASE EXTRACTION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0030694747     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10001-6     Document Type: Article

References (24)

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11. (f) Marx, M. A.; Grillot, A.-L.; Louer, C. T.; Beaver, K. A.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6153-6167. Azomethine ylide cycloadditions with polymer-supported dipolarophiles:
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14. (i) Mjalli, A. M. M.; Sarshar, S.; Baiga, T. J. Tetrahedron Lett 1996, 37, 2943-2946.
15. Pearson, W. H.; Szura, D. P.; Postich, M. J. J. Am. Chem. Soc. 1992, 114, 1329-1345.
16. Pearson, W. H.; Postich, M. J. J. Org. Chem. 1992, 57, 6354-6357.
17. For an overview of the complementarity of 2-azaallyl anions and azomethine ylides, see: Pearson, W. H. In Studies in Natural Products Chemistry. Stereoselective Synthesis (Part A); Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1; pp 323-358.
18. Thompson, L. A.; Ellman, J. A. Tetrahedron Lett. 1994, 35, 9333-9336.
19. (a) Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022.
20. (b) Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272-7276. Swern and pyridine/sulfur trioxide oxidations were also successful, but IBX consistently gave higher yields.
21. Look, G. C.; Murphy, M. M.; Campbell, D. A.; Gallop, M. A. Tetrahedron Lett. 1995, 36, 2937-2940.
22. 1H-NMR experiments and the known tendency of 2-azaallyl anions to give cis-2,5-dialkylpyrrolidines (see ref. 4). However, the degree of certainty of these assignments is not high, as the NOESY data was not unambiguous.
23. The stereochemical assignments were made by comparison to closely related pyrrolidines: Tokuda, M.; Yamada, Y.; Takagi, T.; Suginome, H. Tetrahedron 1987, 43, 281-296.
24. Pearson, W. H.; Jacobs, V. J. Tetrahedron Lett. 1994, 35, 7001-7004.