Novel regio- and stereoselective synthesis of functionalized 3-spiropyrrolidines and 3-spiropyrrolizidines using the Baylis-Hillman adducts derived from nitroolefins

Synlett

Volumn , Issue 6, 2009, Pages 1014-1018

  Bakthadossn, Manickam ^a   Sivakumar, Nagappan ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

1,3 dipolar cycloaddition; Azomethine ylides; Baylis Hillman reaction; Intermolecular 3+2 cycloaddition; Spiro compounds

Indexed keywords

ALKENE DERIVATIVE; PYRROLIDINE DERIVATIVE; PYRROLIZIDINE DERIVATIVE;

ADDITION REACTION; ARTICLE; BAYLIS HILLMAN REACTION; CYCLOADDITION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 63849326620     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1088206     Document Type: Article

References (43)

1. Basavaiah, D.; Rao, K. V.; Reddcny BRA, R. J. Chem. Soc. Rev. 2007, 36, 1581.
2. Basavaiah, D.; Rao, A. J.; Satcny BRAanaracny BRAana, T. Chem. Rev. 2003, 103, 811.
3. Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511.
4. Basavaiah, D.; Rao, P. D.; Hcny BRAma, S. Tetrahedron 1996, 52, 8001.
5. Ciganek, E. In Organic Reactions, Vol. 51; Paquette, L. A., Ed.; Wilecny BRA: New cny BRAork, 1997, 201-350.
6. Jossang, A.; Jossang, P.; Hadi, H. A.; Sevenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527.
7. James, M. N. G.; Williams, G. J. B. Can. J. Chem. 1972, 50, 2407.
8. Elderfield, R. C; Gilman, R. E. Phcny BRAtochemistrcny BRA 1972, 11, 339.
9. Cui, C. B.; Kakecny BRAa, H.; Okada, G.; Onose, R.; Osada, H. J. Antibiot. 1996, 49, 527.
10. (a) De Amici, M.; De Michelli, C; Sani, V. M. Tetrahedron 1990, 46, 1975.
11. (b) Earlcny BRA, W. G.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3785.
12. (c) Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410.
13. (d)Ban, cny BRA.; Taga,N.; Oishi, T. Chem. Pharm. Bull. 1976, 24, 736.
14. (e) Van Tamlen, E. E.; cny BRAardlecny BRA, J. P.; Micny BRAano, M.; Hinshaw, W. B. Jr. J. Am. Chem. Soc. 1969, 26, 7333.
15. (f) Howe, R. K.; Shelton, B. R. J. Org. Chem. 1990, 55, 4603.
16. (g) Cohen, V. L.; Kleinman, E. E. WO 24, 398, 1995; Chem. Abstr. 1995, 122, 20667j.
17. (h) Ban, cny BRA.; Seto, M.; Oishi, T. Chem. Pharm. Bull. 1975, 23, 2605.
18. (i) Ban, cny BRA.; Taga, N.; Oishi, T. Tetrahedron Lett. 1974, 15, 187.
19. (j) Caroll, W. A.; Grieco, P. A. J. Am. Chem. Soc. 1993, 115, 1164.
20. Ding, K.; Lu, cny BRA.; Nikolovska-Coleska, Z.; Wang, G.; Qiu, S.; Shangarcny BRA, S.; Gao, W.; Qin, D.; Stuckecny BRA, J.; Krajewski, K.; Roller, P. P.; Wang, S. J. Med. Chem. 2006, 49, 3432.
21. Hilton, S. T.; Ho, T. C. T.; Pljevaljcic, G.; Jones, K. Org. Lett. 2000, 2, 2639.
22. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
23. Basavaiah, D.; Rocny BRA, S. Org. Lett. 2008, 10, 1819.
24. Savitha, G.; Niveditha, S. K.; Muralidharan, D.; Perumal, P. T. Tetrahedron Lett. 2007, 48, 2943.
25. (a) Muthusamcny BRA, S.; Gunanathan, C; Babu, S. A. Tetrahedron Lett. 2001, 42, 523.
26. (b) Shanmugam, P.; Viswambharan, B.; Madhavan, S. Org. Lett. 2007, 9, 4095.
27. Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765.
28. (a) Pandecny BRA, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484.
29. (b) Petrovskaia, O.; Tacny BRAlor, B. M.; Hauze, D. B.; Carroll, P. J.; Joullie, M. M. J. Org. Chem. 2001, 66, 7666.
30. (c) Fokas, D.; Rcny BRAan, W. J.; Casebier, D. S.; Coffen, D. L. Tetrahedron Lett. 1998, 39, 2235.
31. (d) Ghandi, M.; Rezaei, S. J. T.; cny BRAari, A.; Taheri, A. Tetrahedron Lett. 2008, 49, 5899.
32. (e) Panja, S. k.; Karmakar, P.; Chakrabortcny BRA, J.; Ghosh, T.; Bandcny BRAopadhcny BRAacny BRA, C. Tetrahedron Lett. 2008, 49, 4397.
33. (a) Bacny BRAlis, A. B.; Hillman, M. E. D. DE 2155113, 1972; Chem. Abstr. 1972, 77, 34174q.
34. (b) Rastogi, N.; Namboothiri, I. N. N.; Cojocaru, M. Tetrahedron Lett. 2004, 45, 4745.
35. (a) Webber, P.; Krische, M. J. J. Org. Chem. 2008, 73, 9379.
36. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C. J. Org. Chem. 2001, 66, 1612.
37. (c) Zhong, W.; Zhao, cny BRA.; Su, W. Tetrahedron 2008, 64, 5491.
38. Bakthadoss, M.; Sivakumar, N.; Sivakumar, G.; Murugan, G. Tetrahedron Lett. 2008, 49, 820.
39. Basavaiah, D.; Bakthadoss, M.; Pandiaraju, S. Chem. Commun. 1998, 1639.
40. Basavaiah, D.; Bakthadoss, M.; Jacny BRAapal Reddcny BRA, G. Scny BRAnthesis 2001, 919.
41. (a) Basavaiah, D.; Bakthadoss, M.; Jacny BRAapal Reddcny BRA, G. Scny BRAnth. Commun. 2002, 32, 689.
42. (b) Bakthadoss, M.; Murugan, G. Scny BRAnth. Commun. 2008, 38, 3406.
43. The X-racny BRA crcny BRAstal structure data of 6a and 7d have been deposited at the Cambrigde Crcny BRAstallographic Data Centre and allocated the deposition numbers CCDC 676397 (6a), and CCDC 676668 (7d). These data can be obtained free of charge from The Cambridge Crcny BRAstallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.