KF/Al2O3 mediated 1,3-dipolar cycloaddition of azomethine ylides: a novel and convenient procedure for the synthesis of highly substituted pyrrolidines

Tetrahedron Letters

Volumn 48, Issue 26, 2007, Pages 4535-4537

  Boruah, Monalisa ^a   Konwar, Dilip ^a   Sharma, Saikat Das ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

Azomethine ylide; Cycloaddition reaction; Diastereoselectivity; KF Al2O3; Regioselectivity

Indexed keywords

AZOMETHINE YLIDE; POTASSIUM FLUORIDE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLOADDITION; MICHAEL ADDITION; PROTON TRANSPORT; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34249319405     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.131     Document Type: Article

References (46)

1. Michael J.P. Nat. Prod. Rep. 21 (2004) 625
2. Cheng Y., Huang Z.-T., and Wang M.-X. Curr. Org. Chem. 8 (2004) 325
3. Michael J.P. Alkaloids 55 (2001) 91
4. Notz W., Tanaka F., and Barbas III C.F. Acc. Chem. Res. 37 (2004) 580
5. Obst U., Betschmann P., Lerner C., Seiler P., and Diederich F. Helv. Chim. Acta 83 (2000) 855
6. Alvarez-Ibarra C., Csaky A.G., Lopez I., and Quiroga M.L. J. Org. Chem. 62 (1997) 479
7. Bianco A., Maggini M., Scorrano G., Toniolo C., Marconi G., Villani C., and Prato M. J. Am. Chem. Soc. 118 (1996) 4072
8. Kolodziej S.A., Nikiforovich G.V., Skeean R., Lignon M.F., Martinez J., and Marshall G.R. J. Med. Chem. 38 (1995) 137
9. For recent reviews, see:. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
10. Seayad J., and List B. Org. Biomol. Chem. 3 (2005) 719-724
11. Berkessel A., and Gröger H. Asymmetric Organocatalysis (2005), Wiley-VCH, Weinheim
12. Dell C.P. J. Chem. Soc., Perkin Trans. 1 (1998) 3873
13. Carruthers W. Cycloaddition Reactions in Organic Synthesis (1990), Pergamon Press, Oxford
14. Grigg R. Tetrahedron: Asymmetry 6 (1995) 2475
15. Padwa A. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon Press, Oxford 1069
16. Huisgen R., Scheer W., and Huber H. J. Am. Chem. Soc. 89 (1967) 1753-1755
17. Huisgen R., Scheer W., Szeimies G., and Huber H. Tetrahedron Lett. (1966) 397-404
18. Grigg R., Donegan G., and Gunaratne H.Q.N. Tetrahedron 45 (1989) 1723-1746
19. Grigg R., and Kemp J. J. Chem. Soc., Chem. Commun. (1978) 109-111
20. Huisgen R., Grashey R., and Steingruber E. Tetrahedron Lett. (1963) 1441-1445
21. Grigg R., Montgomery J., and Somasunderam A. Tetrahedron 48 (1992) 10431-10442
22. Grigg R., and Kemp J. J. Chem. Soc., Chem. Commun. (1977) 125
23. Grigg R., and Kemp J. J. Chem. Soc., Chem. Commun. (1978) 109
24. Joucla M., and Hamelin J. Tetrahedron Lett. 19 (1978) 2885
25. Tsuge O., and Ueno K.O. Chem. Lett. (1979) 1407
26. Tasuge O., Kanemasa S., and Yoshioka M. J. Org. Chem. 53 (1988) 1384
27. Allway P., and Grigg R. Tetrahedron Lett. 32 (1991) 5871
28. Longmire M.J., Wang B., and Zhang X. J. Am. Chem. Soc. 124 (2002) 13400
29. Chen C., Li X., and Schreiber S.L. J. Am. Chem. Soc. 125 (2003) 10174
30. Alemart C., Blay G., and Jorgensen K.A. Org. Lett. (2005) 4569
31. Cases J., Grigg R., Najera C., and Sansano J.M. Eur. J. Org. Chem. (2001) 1971
32. Oderatoshi Y., Cheng W., Fujitomi S., Kasano Y., Minakata S., and Komatsu M. Org. Lett. 5 (2003) 5043
33. Blass B.E. Tetrahedron 58 (2002) 9301 and references cited therein
34. Weinstock L.M., Stevenson J.M., Tomellin S.A., Pan S.-H., Utne T., Jobson R.B., and Reinhold D.F. Tetrahedron Lett. 27 (1986) 3845
35. Bunin B.A. The Combinatorial Index (1998), Academic, New York
36. Czarnik A.W., and DeWitt S.H. A Practical Guide to Combinatorial Chemistry (1997), American Chemical Society, Washington, DC
37. Nicolaou K.C., Hanko R., and Hartwig W. Handbook of Combinatorial Chemistry (2002), Wiley-VCH, Weinheim
38. Bougrin K., Soufiaoui M., Loupy A., and Jacquault P. New J. Chem. 19 (1995) 213-219
39. Boruah, M.; Konwar, D. Synthesis, communicated.
40. +). Elemental Anal. Calcd C, 64.98; H, 6.86; N, 5.05%. Found: C, 65.05; H, 6.97; N, 4.85.
41. Stork G., Leong A.Y.W., and Touzin A.M. J. Org. Chem. 41 (1976) 3491
42. Bay P., and Vevert J.P. Tetrahedron Lett. 18 (1977) 1455
43. Fitt J.J., and Gschwend H.W. J. Org. Chem. 42 (1977) 2639
44. Grigg R., Kemp J., Malone J., and Tangthongkum A. J. Org. Chem. (2001) 1971
45. Cases J., Grigg R., Nájera C., and Sansano J.M. Eur. J. Org. Chem. (2001) 1971
46. Texier-Boullet F., Villemin D., Ricard M., Moison H., and Foucaud A. Tetrahedron 41 (1985) 1259