Rate enhancement of the radical 1,2-acyloxy shift (Surzur-Tanner rearrangement) by complexation with Lewis acids

Angewandte Chemie - International Edition

Volumn 37, Issue 16, 1998, Pages 2259-2262

  Lacôte, Emmanuel ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

Aluminum; Lewis acids; Radical reactions; Rearrangements; Scandium

Indexed keywords

EID: 0040561956     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980904)37:16<2259::AID-ANIE2259>3.0.CO;2-U     Document Type: Article

References (43)

1. a) B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, Oxford, 1988;
2. b) W. B. Motherwell, D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992;
3. c) D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996.
4. A. L. J. Beckwith, D. Crich, P. J. Duggan, Q. Yao, Chem. Rev. 1997, 97, 3273-3312.
5. J. M. Surzur, P. Teissier, C. R. Acad. Sci. Fr. Ser. C 1967, 264, 1981-1984.
6. D. D. Tanner, F. C. P. Law, J. Am. Chem. Soc. 1969, 91, 7535-7537.
7. a) L. R. C. Barclay, D. Griller, K. U. Ingold, J. Am. Chem. Soc. 1982, 104, 4399-4403;
8. b) L. R. C. Barclay, J. Lusztyk, K. U. Ingold, J. Am. Chem. Soc. 1984, 106, 1793-1796;
9. c) P. Kocovsky, I. Stary, F. Turecek, Tetrahedron Lett. 1986, 27, 1513-1516;
10. d) H.-G. Korth, R. Sustmann, K. S. Gröninger, M. Leisung, B. Giese, J. Org. Chem. 1988, 53, 4364-4369;
11. e) A. L. J. Beckwith, P. J. Duggan, J. Chem. Soc. Perkin Trans. 2 1992, 1777-1783;
12. f) A. L. J. Beckwith, P. J. Duggan, J. Chem. Soc. Perkin Trans. 2 1993, 1673-1679;
13. g) D. Crich, F. Filzen, J. Org. Chem. 1995, 60, 4834-4837;
14. h) A. L. J. Beckwith, P. J. Duggan, J. Am. Chem. Soc. 1996, 118, 12838-12839;
15. H. Zipse, J. Chem. Soc. Perkin Trans. 2 1997, 1797-1800.
16. a) B. Giese, S. Gilges, K. S. Gröninger, C. Lamberth, T. Witzel, Liebigs Ann. Chem. 1988, 615-617;
17. b) T. Gimisis, G. Ialongo, M. Zamboni, C. Chatgilialoglu, Tetrahedron Lett. 1995, 36, 6781-6784;
18. c) Y. Itoh, K. Haraguchi, H. Tanaka, K. Matsumoto, K. T. Nakamura, T. Miyasaka, Tetrahedron Lett. 1995, 36, 3867-3870.
19. H. Zipse, J. Am. Chem. Soc. 1997, 119, 1087-1093.
20. S. N. Müller, R. Batra, M. Senn, B. Giese, M. Kisel, O. Shadiro, J. Am. Chem. Soc. 1997, 119, 2795-2803.
21. a) P. Renaud, P.-A. Carrupt, M. Gerster, K. Schenk, Tetrahedron Lett. 1994, 35, 1703-1706;
22. b) P. Renaud, N. Moufid, L. H. Kuo, D.P. Curran, J. Org. Chem. 1994, 59, 3547-3552;
23. c) P. Renaud, M. Gerster. J. Am. Chem Soc. 1995, 117, 6607-6608;
24. d) M. Gerster, P. Renaud, Angew. Chem. 1996, 108, 2523-2525; Angew. Chem. Int. Ed. 1996, 35, 2396-2399;
25. d) M. Gerster, P. Renaud, Angew. Chem. 1996, 108, 2523-2525; Angew. Chem. Int. Ed. 1996, 35, 2396-2399;
26. e) M. Gerster, L. Audergon, M. Moufid, P. Renaud, Tetrahedron Lett. 1996, 37, 6335-6338;
27. f) A.-R. Fhal, P. Renaud, Tetrahedron Lett. 1997, 38, 2661-2664.
28. P. Renaud, M. Gerster, Angew. Chem. 1998, 110, in press; Angew. Chem. Int. Ed. 1998, 37, in press.
29. P. Renaud, M. Gerster, Angew. Chem. 1998, 110, in press; Angew. Chem. Int. Ed. 1998, 37, in press.
30. Acceleration of radical cyclizations was recently reported: T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230-1231; Angew. Chem. Int. Ed. 1997, 36, 1181-1183. The rate of cyclization of aminyl radicals is also influenced by Lewis acids: C. Hau, O. M. Musa, F. N. Martinez, M. Newcomb, J. Org. Chem. 1997, 62, 2704-2710; for more examples, see reference [10].
31. Acceleration of radical cyclizations was recently reported: T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230-1231; Angew. Chem. Int. Ed. 1997, 36, 1181-1183. The rate of cyclization of aminyl radicals is also influenced by Lewis acids: C. Hau, O. M. Musa, F. N. Martinez, M. Newcomb, J. Org. Chem. 1997, 62, 2704-2710; for more examples, see reference [10].
32. Acceleration of radical cyclizations was recently reported: T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230-1231; Angew. Chem. Int. Ed. 1997, 36, 1181-1183. The rate of cyclization of aminyl radicals is also influenced by Lewis acids: C. Hau, O. M. Musa, F. N. Martinez, M. Newcomb, J. Org. Chem. 1997, 62, 2704-2710; for more examples, see reference [10].
33. A. L. J. Beckwith, C. B. Thomas, J. Chem. Soc. Perkin Trans. 2 1973, 861-872.
34. The product of phenyl migration (neophyl rearrangement) is not observed under these conditions.
35. [12] For physical data and elemental analysis, see C. S. Marvel, N. S. Moon, J. Am. Chem. Soc. 1940, 62, 45-49.
36. S. Kobayashi, Synlett 1994, 689-701.
37. a) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779-10780;
38. b) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. 1996, 35, 190-192.
39. b) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. 1996, 35, 190-192.
40. In the absence of Lewis acids, the ortho-methoxybenzoate rearranged slightly slower (procedure B: the ratio of rearrangement to direct reduction products was 84:16) than the hydroxy-substituted compound 7 (procedure B: the ratio of rearrangement to direct reduction products was 75:25; Table 1, entry 2). This small difference may be attributed to intramolecular protonation.
41. 3 left the bromide unchanged.
42. A low diastereoselectivity (≤ 60% ds) was observed.
43. Most reported 1,2-acyloxy shifts have been conducted at temperatures higher than 60°C.