Stereoselectivity in the cycloaddition of cyclopentadiene to N-fumaroyl-[2R,S(R)]-bornane-10,2-sulfinamide monomethyl ester

Helvetica Chimica Acta

Volumn 84, Issue 3, 2001, Pages 579-588

  Chapuis, Christian ^a,b   Kawȩcki, Robert ^a   Urbañczyk Lipkowska, Zofia ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b Email:   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CARBON TETRACHLORIDE; CATALYSIS; CATALYST SELECTIVITY; SYNTHESIS (CHEMICAL); TITANIUM COMPOUNDS;

CYCLOADDITION;

ESTERS;

CAMPHOR; CARBON TETRACHLORIDE; CYCLOPENTADIENE DERIVATIVE; ESTER DERIVATIVE; N FUMAROYLBORNANE 10,2 SULFINAMIDE METHYL ESTER; N FUMAROYLSULFINAMIDE; SODIUM BOROHYDRIDE; SULFINAMIDE; TITANIUM TETRACHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035050680     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20010321)84:3<579::AID-HLCA579>3.0.CO;2-Y     Document Type: Article

References (47)

1. M. Achmatowicz, C. Chapuis, P. Rzepecki, J. Jurczak, Helv. Chim. Acta 1999, 82, 182.
2. C. Chapuis, P. Rzepecki, T. Bauer, J. Jurczak, Helv. Chim. Acta 1995, 78, 145.
3. T. Bauer, C. Chapuis, A. Kucharska, P. Rzepecki, J. Jurczak, Helv. Chim. Acta 1998, 81, 324.
4. C. Chapuis, A. Kucharska, P. Rzepecki, J. Jurczak, Helv. Chim. Acta 1998, 81, 2314.
5. M. Virgili, A. Moyano, M. A. Pericas, A. Riera, Tetrahedron 1999, 55, 3959;
6. H. Adams, J. C. Anderson, R. Bell, D. Neville Jones, M. R. Peel, N. C. O. Tomkinson, J. Chem. Soc., Perkin Trans. 1 1998, 3967;
7. S. A. Kozmin, V. H. Rawal, J. Am. Chem. Soc. 1997, 119, 7165.
8. T. Hasegawa, H. Yamamoto, Synlett 1999, 84;
9. J. Duwenhorst, F. P. Monforts, Synlett 1999, 994;
10. W. Schmidt, F. P. Monforts, Synlett 1997, 903;
11. D. P. Becker, R. K. Husa, A. E. Moormann, C. I. Villamil, D. L. Flynn, Tetrahedron 1999, 55, 11787;
12. A. Bernardi, G. Boschin, A. Checchia, M. Lattanzio, L. Manzoni, D. Potenza, C. Scolastico, Eur. J. Org. Chem. 1999, 6, 1311;
13. Y. Abel, E. Haake, G. Haake, W. Schmidt, D. Struve, A. Walter, F. P. Montforts, Helv. Chim. Acta 1998, 81, 1978.
14. T. M. Tarasow, S. L. Tarasow, C. Tu, E. Kellogg, B. E. Eaton, J. Am. Chem. Soc. 1999, 121, 3614;
15. D. A. Evans, S. J. Mayer, T. Lectka, P. Vonmatt, J. Am. Chem. Soc. 1999, 121, 7559;
16. K. Ishihara, K. Inanaga, S. Kondo, M. Funahashi, H. Yamamoto, Synlett 1998, 1053;
17. A. K. Ghosh, H. Cho, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 3687;
18. A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron Lett. 1996, 37, 3815.
19. B. H. Kim, D. P. Curran, Tetrahedron 1993, 49, 293.
20. a) C. Chapuis, J. Y. de Saint Laumer, presented at the 'IX ESOC', Warsaw, Poland, 18-23 June, 1995;
21. b) T. Bauer, C. Chapuis, A. Jezewski, J. Kozak, J. Jurczak, Tetrahedron: Asymmetry 1996, 7, 1391;
22. c) T. Bauer, C. Chapuis, J. Kiegiel, J. W. Krajewski, K. Piechota, Z. Urbañczyk-Lipkowska, J. Jurczak, Helv. Chim. Acta 1996, 79, 1059;
23. d) C. Chapuis, J.-Y. de Saint Laumer, M. Marty, Helv. Chim. Acta 1997, 80, 146;
24. e) G. Bernardinelli, C. Chapuis, A. Kingma, M. Wills, Helv. Chim. Acta 1997, 80, 1607.
25. R. Kawecki, Tetrahedron: Asymmetry 1999, 10, 4183.
26. J. Kiegiel, C. Chapuis, Z. Urbañczyk-Lipkowska, J. Jurczak, Helv. Chim. Acta 1998, 81, 1672.
27. G. Wagner, R. Herrmann, A. Schier, J. Chem. Soc., Perkin Trans. 1 1997, 701.
28. J. J. P. Stewart, J. Comput.-Aided Mol. Design 1990, 4, 1.
29. W. Oppolzer, J.-P. Barras, Helv. Chim. Acta 1987, 70, 1666.
30. W. Oppolzer, C. Chapuis, G. Bernardinelli, Helv. Chim. Acta 1984, 67, 1397.
31. J. Raczko, M. Achmatowicz, A. Jezewski, C. Chapuis, Z. Urbañczyk-Lipkowska, J. Jurczak, Helv. Chim. Acta 1998, 81, 1264.
32. C. Thom, P. Kocienski, Synthesis 1992, 582;
33. R. S. Ward, A. Pelter, D. Goubet, M. C. Pritchard, Tetrahedron: Asymmetry 1995, 6, 469.
34. C. Chapuis, A. Kucharska, J. Jurczak, Tetrahedron: Asymmetry 2000, 11, 4581;
35. th Electronic Conference on Synthetic Organic Chemistry', September 1-30, 2000, Basel, http://www.uni-bas.ch/mdpi/ecsoc-4.htm, poster # a0037; available at http://reprints.net/ecsoc-4/a0037/a0037.htm.
36. D. Horton, T. Machinami, J. Chem. Soc., Chem. Commun. 1981, 88;
37. D. Horton, T. Machinami, Y. Takagi, Carbohydrate Res. 1983, 121, 135;
38. S. Takano, A. Kurotaki, K. Ogasawara, Synthesis 1987, 1075;
39. S. Saito, H. Hama, Y. Matsuura, K. Okada, T. Moriwake, Synlett 1991, 819.
40. W. Oppolzer, I. Rodriguez, J. Blagg, G. Bernardinelli, Helv. Chim. Acta 1989, 72, 123.
41. W. Oppolzer, Tetrahedron 1987, 43, 1969; erratum, Tetrahedron. 1987, 43, 4057.
42. J. Raczko, M. Achmatowicz, P. Kwiatkowski, C. Chapuis, Z. Urbañczyk-Lipkowska, J. Jurczak, Tetrahedron: Asymmetry 2000, 11, 1027.
43. H. D. Flack, Acta Crystallogr., Sect. C 1983, 39, 876;
44. H. D. Flack, G. Bernardinelli, Acta Crystallogr., Sect. A 1999, 55, 908;
45. H. D. Flack, G. Bernardinelli, J. Appl. Crystallogr. 2000, 33, 1143.
46. G. M. Sheldrick, 'SHELX86, Program for the Solution of Crystal Structures', University of Göttingen, Germany, 1985.
47. G. M. Sheldrick, 'SHELX93, Program for the Refinement of Crystal Structures', University of Göttingen, Germany, 1993.