Radical cyclization/β-elimination tandem reactions: Enantiopure sulfoxides as temporary chiral auxiliaries

Angewandte Chemie - International Edition

Volumn 37, Issue 15, 1998, Pages 2116-2118

  Lacôte, Emmanuel ^a   Delouvrié, Bénédicte ^a   Fensterbank, Louis ^a   Malacria, Max ^a  

^a CNRS   (France)

Author keywords

Asymmetric synthesis; Cyclizations; Domino reactions; Lewis acids; Radicals

Indexed keywords

EID: 0041968056     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980817)37:15<2116::AID-ANIE2116>3.0.CO;2-L     Document Type: Article

References (33)

1. B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K. J. Kulicke, F. Trach, Org. React. (N.Y.) 1996, 48, 301-856.
2. D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996.
3. a) N. A. Porter, B. Lacher, V. H.-T. Chang, D. R. Magnin, J. Am. Chem. Soc 1989, 111, 8309-8310;
4. b) N. A. Porter, D.M. Scott, B. Lacher, B. Giese, H. G. Zeitz, H. J. Lindner, J. Am. Chem. Soc. 1989, 111, 8311-8312;
5. c) D. M. Scott, A. T. McPhail, N. A. Porter, Tetrahedron Lett. 1990, 31, 1679-1682;
6. d) N. A. Porter, D. M. Scott, I. J. Rosenstein, B. Giese, A. Veit, H. G. Zeitz, J. Am. Chem. Soc. 1991, 113, 1791-1799.
7. a) J. G. Stack, D. P. Curran, S. V. Geib, J. Rebek, Jr., P. Ballester, J. Am. Chem. Soc. 1992, 114, 7007-7018;
8. b) K. Rück, H. Kunz, Synlett 1992, 343-344;
9. c) M. Zahouily, M. Journet, M. Malacria, Synlett. 1994, 366-368;
10. d) N. Mase, Y. Watanabe, Y. Ueno, T. Toru, J. Org. Chem. 1997, 62, 7794-7800.
11. a) Review: R. Renaud, M. Gerster, Angew. Chem. 1998, 110, in press; Angew. Chem. Int. Ed. 1998, 37, in press;
12. a) Review: R. Renaud, M. Gerster, Angew. Chem. 1998, 110, in press; Angew. Chem. Int. Ed. 1998, 37, in press;
13. b) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, J. Am. Chem. Soc. 1994, 116, 6455-6456;
14. c) M. Nishida, A. Nishida, N. Kawahara, J. Org. Chem. 1996, 61, 3574-3575.
15. M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779-10780.
16. E. Lacôte, M. Malacria, C. R. Acad. Sci. Fr., Ser. IIc 1998, 191-194.
17. a) T. E. Boothe, J. L. Greene, Jr., P. B. Shevlin, M. R. Willcott III, R. R. Inners, A. Cornelis, J. Am. Chem. Soc. 1978, 100, 3874-3879;
18. b) G. A. Russell, H. Tashtoush, P. Ngoviwatchai, J. Am. Chem. Soc. 1984, 106, 4622-4623; other representative addition-elimination sequences with vinyl sulfones:
19. c) J. R. McCarthy, E. W. Huber, T.-B. Le, F. M. Laskovics, D. P. Matthews, Tetrahedron 1996, 52, 45-58;
20. d) S. Caddick, C. L. Shering, S. N. Wadman, Tetrahedron Lett. 1997, 38, 6249-6250;
21. e) F. Aldabbagh, W. R. Bowman, Tetrahedron Lett. 1997, 38, 3793-3794; vinylsulfimides:
22. f) A. J. Clark, S. Rooke, T. J. Sparey, P. C. Taylor, Tetrahedron Lett. 1996, 37, 909-912; vinyltrifluoromethylsulfones:
23. g) J. Xiang, P. L. Fuchs, J. Am. Chem. Soc. 1996, 118, 11986-11987.
24. Malonate 4 was obtained in 50-60% yield by the addition of phenylselenyl chloride in methanol onto prenyl dimethylmalonate: D. G. Garratt, A. Kabo, Can. J. Chem. 1980, 58, 1030-1041.
25. Allyl bromides 5a, 5c, and 5d: E. Bonfand, P. Gosselin, C. Maignan, Tetrahedron: Asymmetry 1993, 4, 1667-1676. Bromide 5b was prepared by the same procedure.
26. K. Nozaki, K. Oshima, K. Utimoto, J. Am. Chem. Soc. 1987, 109, 2547-2549.
27. The determination of the enantiomeric excesses was performed on the diols 8 with the chiral phosphorus derivatives method of Alexakis and Mangeney: A. Alexakis, J. C. Frutos, S. Mutti, P. Mangeney, J. Org. Chem. 1994, 59, 3326-3334.
28. P. J. Wagner, J. H. Sedon, M. J. Lindstrom, J. Am. Chem. Soc. 1978, 100, 2579-2580.
29. M. Newcomb, Tetrahedron 1993, 49, 1151-1176.
30. Review: R. W. Hoffmann, Chem. Rev. 1989, 89, 1841-1860.
31. 2).
32. 2).
33. 2).