A simple and flexible synthesis of pyrroles from α,β-unsaturated sulfones;Eine einfache und flexible synthese von pyrrolen aus α,β- ungesattigten sulfonen

Helvetica Chimica Acta

Volumn 81, Issue 11, 1998, Pages 1978-1996

  Abel, Yvonne ^a   Haake, Elmar ^a   Haake, Gerold ^a,b   Schmidt, Wolfgang ^a,c   Struve, Daria ^a,d   Walter, Andreas ^a   Montforts, Franz Peter ^a  

^a UNIVERSITY OF BREMEN   (Germany)

^b Knoll AG   (Germany)

^c UNIVERSITY OF INNSBRUCK   (Austria)

^d Grillo Werke AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ISOCYANOACETONITRILE; NITRILE; PYRROLE DERIVATIVE; SULFONE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0031758289     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1522-2675(19981111)81:11<1978::aid-hlca1978>3.0.co;2-t     Document Type: Article

References (50)

1. G. Haake, D. Struve, F.-P. Montforts, Tetrahedron Lett. 1994, 35, 9703; Y. Abel, F.-P. Montforts, ibid. 1997, 38, 1745; W. Schmidt, F.-P. Montforts, Synlett 1997, 903.
2. G. Haake, D. Struve, F.-P. Montforts, Tetrahedron Lett. 1994, 35, 9703; Y. Abel, F.-P. Montforts, ibid. 1997, 38, 1745; W. Schmidt, F.-P. Montforts, Synlett 1997, 903.
3. G. Haake, D. Struve, F.-P. Montforts, Tetrahedron Lett. 1994, 35, 9703; Y. Abel, F.-P. Montforts, ibid. 1997, 38, 1745; W. Schmidt, F.-P. Montforts, Synlett 1997, 903.
4. F.-P. Montforts, M. Glasenapp-Breiling, D. Kusch, in 'Houben-Weyl, Methods of Organic Chemistry', Ed. E. Schaumann, Thieme, Stuttgart - New York, 1998, Vol. E9 d, S. 577-716.
5. F.-P. Montforts, B. Gerlach, F. Höper, Chem. Rev. 1994, 94, 327.
6. F.-P. Montforts, M. Glasenapp-Breiling, in 'Progress in Heterocylic Chemistry', Eds. G. W. Gribble und T. L. Gilchrist, Oxford, 1998, Vol. 10, im Druck.
7. A. Eschenmoser, Angew. Chem. 1988, 100, 5; ibid., Int. Ed. Engl. 1988, 27, 5.
8. A. Eschenmoser, Angew. Chem. 1988, 100, 5; ibid., Int. Ed. Engl. 1988, 27, 5.
9. H. Falk, 'The Chemistry of Linear Oligopyrroles and Bile Pigments', Springer, Wien, 1989.
10. J. L. Sessler, S. J. Weghorn, 'Expanded, Contracted and Isomeric Porphyrins', Pergamon Press, Oxford, 1997.
11. D. Dolphin, A. Jasat, Chem. Rev. 1997, 97, 2267.
12. A. Gossauer, 'Die Chemie der Pyrrole', Springer, Berlin, 1974.
13. R. A. Jones, G. P. Bean, 'The Chemistry of Pyrroles', Academic Press, London, 1977.
14. A. M. van Leusen, H. Siderius, B. E. Hoogenboom, D. van Leusen, Tetrahedron Lett. 1972, 52, 5337; A. M. van Leusen, R. J. Bouma, O. Possel, ibid. 1975, 40, 3487; H. A. Houwing, J. Wildeman, A. M. van Leusen, ibid. 1976, 2, 143.
15. A. M. van Leusen, H. Siderius, B. E. Hoogenboom, D. van Leusen, Tetrahedron Lett. 1972, 52, 5337; A. M. van Leusen, R. J. Bouma, O. Possel, ibid. 1975, 40, 3487; H. A. Houwing, J. Wildeman, A. M. van Leusen, ibid. 1976, 2, 143.
16. A. M. van Leusen, H. Siderius, B. E. Hoogenboom, D. van Leusen, Tetrahedron Lett. 1972, 52, 5337; A. M. van Leusen, R. J. Bouma, O. Possel, ibid. 1975, 40, 3487; H. A. Houwing, J. Wildeman, A. M. van Leusen, ibid. 1976, 2, 143.
17. D. Barton, S. Zard, J. Chem. Soc., Chem. Commun. 1985, 1098; D. Barton, J. Kervagoret, S. Zard, Tetrahedron 1990, 46, 7587.
18. D. Barton, S. Zard, J. Chem. Soc., Chem. Commun. 1985, 1098; D. Barton, J. Kervagoret, S. Zard, Tetrahedron 1990, 46, 7587.
19. U. Schöllkopf, Angew. Chem. 1977, 89, 351; ibid., Int. Ed. Engl. 1977, 16, 339.
20. U. Schöllkopf, Angew. Chem. 1977, 89, 351; ibid., Int. Ed. Engl. 1977, 16, 339.
21. D. Hoppe, Angew. Chem. 1974, 86, 878; ibid., Int. Ed. Engl. 1974, 13, 789.
22. D. Hoppe, Angew. Chem. 1974, 86, 878; ibid., Int. Ed. Engl. 1974, 13, 789.
23. P. Magnus, P. Halazy, Tetrahedron Lett. 1984, 25, 1421.
24. D. P. Arnold, L. Burgess-Dean, J. Hubbard, M. A. Rahman, Aust. J. Chem. 1994, 35, 969.
25. S. Ito, T. Murashima, N. Ono, J. Chem. Soc., Perkin Trans. 1 1997, 3161.
26. N. S. Simpkins, 'Sulfones in Organic Chemistry', Pergamon Press, Oxford, 1993.
27. G. Helmchen, A. F. Abdel Hady, H. Hartmann, R. Karge, A. Krotz, K. Sartor, M. Urmann, Pure Appl. Chem. 1989, 61, 409; A. F. Abdel Hady, Dissertation, Universität Heidelberg; wir danken Prof. G. Helmchen (Heidelberg), für die Überlassung von Original-Versuchsvorschriften.
28. G. Helmchen, A. F. Abdel Hady, H. Hartmann, R. Karge, A. Krotz, K. Sartor, M. Urmann, Pure Appl. Chem. 1989, 61, 409; A. F. Abdel Hady, Dissertation, Universität Heidelberg; wir danken Prof. G. Helmchen (Heidelberg), für die Überlassung von Original-Versuchsvorschriften.
29. K. C. Nicolaou, S. P. Seitz, W. J. Sipio, J. F. Blount, J. Am. Chem. Soc. 1979, 101, 3884; H. Müller, P. E. Butler, ibid. 1968, 90, 2075.
30. K. C. Nicolaou, S. P. Seitz, W. J. Sipio, J. F. Blount, J. Am. Chem. Soc. 1979, 101, 3884; H. Müller, P. E. Butler, ibid. 1968, 90, 2075.
31. H. Wissmann, H. J. Kleiner, Angew. Chem. 1980, 92, 129; ibid., Int. Ed. Engl. 1980, 19, 133.
32. H. Wissmann, H. J. Kleiner, Angew. Chem. 1980, 92, 129; ibid., Int. Ed. Engl. 1980, 19, 133.
33. D. Liotta, U. Sunay, H. Santiestban, W. Markiewicz, J. Org. Chem. 1981, 46, 2605; R. M. Scarborough, A. B. Smith, Tetrahedron Lett. 1977, 50, 4361.
34. D. Liotta, U. Sunay, H. Santiestban, W. Markiewicz, J. Org. Chem. 1981, 46, 2605; R. M. Scarborough, A. B. Smith, Tetrahedron Lett. 1977, 50, 4361.
35. R. Appel, Angew. Chem. 1975, 87, 863; ibid., Int. Ed. Engl. 1975, 14, 801.
36. R. Appel, Angew. Chem. 1975, 87, 863; ibid., Int. Ed. Engl. 1975, 14, 801.
37. J. Buschmann, D. Lentz, P. Luger, G. Perpetuo, D. Scharn, S. Willemsen, Angew. Chem. 1995, 107, 988; ibid., Int. Ed. Engl. 1995, 34, 914.
38. J. Buschmann, D. Lentz, P. Luger, G. Perpetuo, D. Scharn, S. Willemsen, Angew. Chem. 1995, 107, 988; ibid., Int. Ed. Engl. 1995, 34, 914.
39. D. Gust, T. A. Moore, A. L. Moore, G. Seely, P. Liddell, D. Barrett, L. O. Harding, X. C. Ma, S.-J. Lee, F. Gao, Tetrahedron 1989, 45, 4867.
40. U. Seitz, J. Daub, Synthesis 1986, 686.
41. K. M. Barkingia, L. Chantrnupomg, K. M. Smith, J. Fajer, J. Am. Chem. Soc. 1988, 110, 7566; K. M. Barkingia, M. D. Berber, J. Fajer, C. J. Medforth, M. W. Renner, K. M. Smith, ibid. 1990, 112, 8851; W. Jentzen, M. C. Simpson, J. D. Hobbs, X. Song, T. Ema, N. Y. Nelson, C. D. Medforth, K. M. Smith, M. Veyrat, M. Mazzanti, R. Ramasseul, J. C. Marchon, T. Takeuchi, W. A. Goddard, J. A. Shelnutt, ibid. 1995, 117, 11805.
42. K. M. Barkingia, L. Chantrnupomg, K. M. Smith, J. Fajer, J. Am. Chem. Soc. 1988, 110, 7566; K. M. Barkingia, M. D. Berber, J. Fajer, C. J. Medforth, M. W. Renner, K. M. Smith, ibid. 1990, 112, 8851; W. Jentzen, M. C. Simpson, J. D. Hobbs, X. Song, T. Ema, N. Y. Nelson, C. D. Medforth, K. M. Smith, M. Veyrat, M. Mazzanti, R. Ramasseul, J. C. Marchon, T. Takeuchi, W. A. Goddard, J. A. Shelnutt, ibid. 1995, 117, 11805.
43. K. M. Barkingia, L. Chantrnupomg, K. M. Smith, J. Fajer, J. Am. Chem. Soc. 1988, 110, 7566; K. M. Barkingia, M. D. Berber, J. Fajer, C. J. Medforth, M. W. Renner, K. M. Smith, ibid. 1990, 112, 8851; W. Jentzen, M. C. Simpson, J. D. Hobbs, X. Song, T. Ema, N. Y. Nelson, C. D. Medforth, K. M. Smith, M. Veyrat, M. Mazzanti, R. Ramasseul, J. C. Marchon, T. Takeuchi, W. A. Goddard, J. A. Shelnutt, ibid. 1995, 117, 11805.
44. S. R. Wilson, D. P. Wiesler, Synth. Commun. 1980, 10, 339.
45. a) K. Ando, M. Kankake, T. Suzuki, H. Takayama, Synlett 1994, 9, 741;
46. b) M. G. H. Vicente, A. C. Tomé, A. Walter, J. A. S. Cavaleiro, Tetrahedron Lett. 1997, 38, 3639.
47. P. B. Hopkins, P. C. Fuchs, J. Org. Chem. 1978, 43, 1209; B. M. Trost, D. P. Curran, Tetrahedron Lett. 1981, 22, 1287; S.-S. P. Chou, C. M. Sun, ibid. 1990, 35, 1035.
48. P. B. Hopkins, P. C. Fuchs, J. Org. Chem. 1978, 43, 1209; B. M. Trost, D. P. Curran, Tetrahedron Lett. 1981, 22, 1287; S.-S. P. Chou, C. M. Sun, ibid. 1990, 35, 1035.
49. P. B. Hopkins, P. C. Fuchs, J. Org. Chem. 1978, 43, 1209; B. M. Trost, D. P. Curran, Tetrahedron Lett. 1981, 22, 1287; S.-S. P. Chou, C. M. Sun, ibid. 1990, 35, 1035.
50. D. H. Burns, C. S. Jabara, M. W. Burden, Synth. Commun. 1995, 25, 379.