Aza-[3,3]-Claisen enolate rearrangement in vinylaziridines: Stereoselective synthesis of mono-, di-, and trisubstituted seven-membered lactams

Chemistry - A European Journal

Volumn 7, Issue 1, 2001, Pages 94-98

  Lindström, Ulf M ^a   Somfai, Peter ^b  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

C c coupling; Lactams; Rearrangements; Vinylaziridines

Indexed keywords

AZIRIDINE DERIVATIVE; LACTAM; LACTAM DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLAZIRIDINE DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONFORMATION; DRUG DESIGN; KINETICS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS; TEMPERATURE;

AZIRIDINES; DRUG DESIGN; KINETICS; LACTAMS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0035808295     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010105)7:1<94::AID-CHEM94>3.0.CO;2-M     Document Type: Article

References (45)

1. T. Nakai, K. Mikami, Org. React. NY 1994, 46, 105.
2. J. A. Marshall in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 975.
3. K. Mikami, T. Nakai, Synthesis 1991, 594.
4. D. Enders, M. Knopp, R. Schiffers, Tetrahedron: Asymmetry 1996, 7, 1847.
5. H. Frauenrath in Houben-Weyl E 21, Vol. 6 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1996, Chapter 1.6.3.1.
6. S. Pereira, M. Srebnik, Aldrichimica Acta 1993, 26, 17.
7. P. Wipf in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 827.
8. R. K. Hill in Asymmetric Synthesis, Vol. 4 (Ed.: J. D. Morrison), Academic, Orlando, 1984, Chapter 8.
9. P. Scheiner, J. Org. Chem. 1967, 32, 2628.
10. I. Coldham, A. J. Collis, R. J. Mould, R. E. Rathmell, J. Chem. Soc. Perkin Trans. 1 1995, 2739.
11. L. Viallon, O. Reinaud, P. Capdevielle, M. Maumy, Tetrahedron Lett. 1995, 36, 4787.
12. J. Åhman, T. Jarevång, P. Somfai, J. Org. Chem. 1996, 61, 8148.
13. G. W. Spears, K. Nakanishi, Y. Ohfune, Synlett 1991, 91.
14. D. Tanner, P. Somfai, Tetrahedron Lett. 1987, 28, 1211.
15. T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, N. Fujii, N. Mimura, Y. Miwa, T. Taga, Y. Yamamoto, Angew. Chem. 1994, 106, 693; Angew. Chem. Int. Ed. Engl. 1994, 33, 652.
16. T. Ibuka, K. Nakai, H. Habashita, Y. Hotta, N. Fujii, N. Mimura, Y. Miwa, T. Taga, Y. Yamamoto, Angew. Chem. 1994, 106, 693; Angew. Chem. Int. Ed. Engl. 1994, 33, 652.
17. P. Wipf, P. C. Fritch, J. Org. Chem. 1994, 59, 4875.
18. G. Cardillo, M. Orena, S. Sandri, C. Tomasini, Tetrahedron 1986, 42, 917.
19. For a general discussion, see: Strain-Assisted Syntheses Tetrahedron Symposia-in-Print (Ed.: L. Ghosez), Tetrahedron 1989, 45, 2875.
20. T. Hudlicky, J. W. Reed in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 899.
21. H. Aoyama, N. Mimura, H. Ohno, K. Ishii, A. Toda, H. Tamamura, A. Otaka, N. Fujii, T. Ibuka, Tetrahedron Lett. 1997, 38, 7383.
22. T. Hudlicky, G. Seoane, J. D. Price, K. G. Gadamasetti, Synlett 1990, 433.
23. J. Åhman, P. Somfai, J. Am. Chem. Soc. 1994, 116, 9781.
24. C. Vogel, Synthesis 1997, 497.
25. J. Åhman, P. Somfai, Tetrahedron 1995, 51, 9747.
26. P. Somfai, T. Jarevång, U. M. Lindström, A. Svensson, Acta Chem. Scand. 1997, 51, 1024.
27. P. Somfai, J. Åhman, Tetrahedron Lett. 1995, 36, 1953.
28. T. Hudlicky, J. O. Frazier, G. Seoane, M. Tiedje, A. Seoane, L. D. Kwart, C. Beal, J. Am. Chem. Soc. 1986, 108, 3755.
29. W. H. Pearson, Tetrahedron Lett. 1985, 26, 3527.
30. U. M. Lindström, P. Somfai, Synthesis 1998, 109.
31. D. Díez-Martin, N. R. Kotecha, S. L. Ley, S. Mantegani, J. C. Menéndez, H. Organ, A. D. White, J. B. Banks, Tetrahedron 1992, 48, 7899.
32. M. Frohn, M. Dalkiewicz, Y. Tu, Z.-X. Wang, Y. Shi, J. Org. Chem. 1998, 63, 2948.
33. U. M. Lindström, B. Olofsson, P. Somfai, Tetrahedron Lett. 1999, 40, 9273.
34. U. M. Lindström, P. Somfai, J. Am. Chem. Soc. 1997, 119, 8385.
35. P. A. Evans, A. B. Holmes, Tetrahedron 1991, 47, 9131.
36. K. Furness, J. Aubé, Org. Lett. 1999, 1, 495.
37. A. D. Piscopio, J. F. Miller, K. Koch, Tetrahedron Lett. 1998, 39, 2667.
38. J. Pernerstorfer, M. Schuster, S. Blechert, Synthesis 1998, 138.
39. G. R. Proctor, J. Redpath in The Chemistry of Heterocyclic Compounds, Vol. 56 (Ed.: E. C. Taylor), Wiley, Chichester, 1996.
40. R. M. Freidinger, D. S. Perlow, D. E Veber, J. R. Brooks, R. Saperstein, Science 1980, 210, 656.
41. S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789.
42. D. Tanner, C. Birgersson, A. Gogoll, K. Luthman, Tetrahedron 1994, 50, 9779.
43. D. A. Evans, J. V. Nelson, T. R. Taber in Topics in Stereochemistry, Vol. 13 (Eds.: N. L. Allinger, E. L. Eliel, S. H. Wilen), Wiley, New York, 1982, p. 1.
44. CS Chem3D Pro (MM2), 3.5 ed., CambridgeSoft, Cambridge, 1997.
45. A. Giovannini, D. Savoia, A. Umani-Ronchi, J. Org. Chem. 1989, 54, 228.