Synthetic studies on the MARDi cascade: Stereoselective preparation of sulfonyl-substituted seven-membered rings

Synlett

Volumn , Issue 17, 2006, Pages 2751-2754

  Coquerel, Yoann ^a   Bensa, David ^a   Moret, Vincent ^a   Rodriguez, Jean ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Cycloheptane; Domino reactions; Multicomponent reactions; Ring expansion; Stereoselective synthesis

Indexed keywords

2 BENZENESULFONYL CYCLOPENTANONE; CYCLOHEPTANE DERIVATIVE; CYCLOPENTANONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 33750519266     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950261     Document Type: Article

References (20)

1. (a) Rodriguez, J. Synlett 1999, 505.
2. (b) Simon, C.; Constantieux, T.; Rodriguez, J. Eur. J. Org. Chem. 2004, 4957.
3. (c) Liéby-Muller, F.; Simon, C.; Constantieux, T.; Rodriguez, J. QSAR Comb. Sci. 2006, 25, 432.
4. (a) Filippini, M.-H.; Rodriguez, J.; Santelli, M. J. Chem. Soc., Chem. Commun. 1993, 1647.
5. (b) Filippini, M.-H.; Rodriguez, J. J. Org. Chem. 1997, 62, 3034.
6. (c) The structure of the cycloheptenic acids 3 has been reviewed and confirmed to be as depicted in Scheme 1 by X-ray diffraction analysis of the derivative A (Scheme 3; see ref. 9). The full detailed study of the MARDi cascade will be reported in due time.
7. (a) Filippini, M.-H.; Rodriguez, J. Chem. Rev. 1999, 99, 27.
8. (b) Filippini, M.-H.; Faure, R.; Rodriguez, J. J. Org. Chem. 1995, 60, 6872.
9. For reviews, see: (a) Yet, L. Tetrahedron 1999, 55, 9349.
10. (b) Yet, L. Chem. Rev. 2000, 100, 2963.
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12. (d) Maier, M. E. Angew. Chem. Int. Ed. 2000, 39, 2073.
13. For examples of sulfonyl-substituted cycloheptanes, see: (e) Arjona, O.; de Dios, A.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem. 1994, 59, 3906.
14. (f) Arjona, O.; Plumet, J. Curr. Org. Chem. 2002, 6, 571.
15. (g) El-Awa, A.; Fuchs, P. Org. Lett. 2006, 8, 2905.
16. Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976, 98, 4887.
17. Carreño, M. C.; García Ruano, J. L.; Pedregal, C.; Rubio, A. J. Chem. Soc., Perkin Trans. 1 1989, 1335.
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19. Hashimoto, N.; Aoyama, T.; Shiori, T. Chem. Pharm. Bull. 1981, 29, 1475.
20. Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, with CCDC numbers 615710, 615708, 615709 for compounds A, 8 and 9, respectively. Copies of this information can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac. uk or www: http://www.ccdc.cam.ac.uk].