Preparation of fused polycyclic vinylcyclopropanes via radical cascade reactions

Chemical Communications

Volumn , Issue 9, 2007, Pages 936-938

  Maddess, Matthew L ^a   Mainetti, Emily ^a   Harrak, Youssef ^a   Brancour, Célia ^a   Devin, Priscille ^a   Dhimane, Anne Lise ^a   Fensterbank, Louis ^a   Malacria, Max ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; CYCLOPROPANE DERIVATIVE; DICHLOROMETHYL DIMETHYLSILYL ETHER; ETHER DERIVATIVE; UNCLASSIFIED DRUG; VINYLCYCLOPROPANE;

ARTICLE; CHEMICAL REACTION; ELIMINATION REACTION; RADICAL REACTION; REACTOR CASCADE;

EID: 33847201133     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b618156b     Document Type: Article

References (43)

1. Radicals in Organic Synthesis, ed., P. Renaud, and, M. P. Sibi,, Wiley-VCH, Weinheim, 2001, vol. 1 & 2
2. W. B. Motherwell and D. Crich, in Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992
3. L. F. Tietze, G. Brasche and K. M. Gericke, in Domino Reactions in Organic Synthesis, Wiley-VCH, Weiheim, 2006
4. M. Albert L. Fensterbank E. Lacôte M. Malacria Top. Curr. Chem. 2006 264 1
5. A. L. J. Beckwith and K. U. Ingold, in Rearrangements in Ground and Excited States, ed., P. de Mayo,, Academic Press, New York, 1980, vol. 1, pp. 162-310
6. B. Maillard D. Forrest K. U. Ingold J. Am. Chem. Soc. 1976 98 7024
7. T. A. Halgren J. D. Roberts J. H. Horner F. N. Martinez C. Tronche M. Newcomb J. Am. Chem. Soc. 2000 122 2988
8. M. Newcomb Tetrahedron 1993 49 1151
9. D. C. Nonhebel Chem. Soc. Rev. 1993 347
10. C. R. Warner R. J. Strunk H. G. Kuivila J. Org. Chem. 1966 31 3381
11. V. M. Bowry J. Lusztyk K. U. Ingold J. Chem. Soc., Chem. Commun. 1990 923
12. R. N. Saicic Z. Cekovic Tetrahedron 1992 48 8975
13. P. Devin L. Fensterbank M. Malacria J. Org. Chem. 1998 63 6764
14. W.-W. Weng T.-Y. Luh J. Org. Chem. 1993 58 5574
15. A. Srikrishna R. Viswajanani T. J. Reddy D. Vijaykumar P. P. Kumar J. Org. Chem. 1997 62 5232
16. M. Journet M. Malacria J. Org. Chem. 1994 59 718
17. R. Zriba S. Bezzenine-Laffolée F. Guibé M.-G. Guillerez Synlett 2005 2362
18. B. Delouvrié L. Fensterbank E. Lacôte M. Malacria J. Am. Chem. Soc. 1999 121 11395
19. D. Leca K. Song M. Albert M. G. Gonçalves L. Fensterbank E. Lacôte M. Malacria Synthesis 2005 1405
20. L. Fensterbank M. Malacria S. M. Sieburth Synthesis 1997 8 813
21. C. Aïssa B. Delouvrié A.-L. Dhimane L. Fensterbank M. Malacria Pure Appl. Chem. 2000 72 1605
22. K. Tamao K. Nagata Y. Ito K. Maeda M. Shiro Synlett 1994 257
23. Y. Nishii A. Fujiwara K. Wakasugi M. Miki K. Yanagi Y. Tanabe Chem. Lett. 2002 30
24. C. C. Huval D. A. Singleton Tetrahedron Lett. 1993 34 3041
25. G. A. Kraus B. Andersh Q. Su J. Shi Tetrahedron Lett. 1993 34 1741
26. S. Kim N. Kim W.-j. Chung C. H. Cho Synlett 2001 937
27. J. M. Tanko M. Sadeghipour Angew. Chem., Int. Ed. 1999 38 159
28. (Dichloromethyl)dimethylchlorosilane is available from Alfa Aesar™ (50 g, $139.00)
29. V. Mamane T. Gress H. Krause A. Fürstner J. Am. Chem. Soc. 2004 126 8654
30. H. E. Paaren H. F. DeLuca K. S. Heinrich J. Org. Chem. 1980 45 3253
31. A. Kutner K. L. Perlman A. Lago R. R. Sicinski H. K. Schnoes H. F. DeLuca J. Org. Chem. 1988 53 3450
32. H. S. Gill J. M. Londowski R. A. Corrandino A. R. Zinsmeister R. Kumar J. Med. Chem. 1990 33 480
33. M. Journet M. Malacria J. Org. Chem. 1992 57 3085
34. D. P. Curran and N. A. Porter, in Stereochemistry of Radical Reactions, Wiley-VCH, Weinheim, 2001, pp. 30-115
35. J. W. Wilt F. G. Belmonte P. A. Zieske J. Am. Chem. Soc. 1983 105 5665
36. K. W. Krosley G. J. Gleicher G. E. Clapp J. Org. Chem. 1992 57 840
37. D. J. Carlsson K. U. Ingold J. Am. Chem. Soc. 1968 90 7047
38. G. R. Jones Y. Landais Tetrahedron 1996 52 7599
39. S. E. Denmark S.-M. Yang Org. Lett. 2001 3 1749
40. NMR yield based on 60% of conversion
41. S. Bogen M. Gulea L. Fensterbank M. Malacria J. Org. Chem. 1999 64 4920
42. E. Mainetti L. Fensterbank M. Malacria Synlett 2002 923
43. As suggested by a referee, alternative reaction channels are open such as an initial 6-exo-trig cyclization, or a 1,5-H transfer from the allylic methylene group. We have not so far isolated products bringing evidence for such pathways. We thank the referee for this suggestion