Stereoselective intramolecular oxime olefin cycloadditions involving carbohydrate derived precursors

Synlett

Volumn , Issue 12, 1998, Pages 1333-1334

  Moutel, Stéphane ^a   Shipman, Michael ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001843116     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1969     Document Type: Article

References (21)

1. Oppolzer, W.; Keller, K. Tetrahedron Lett., 1970, 1117.
2. Slabaugh, M.R.; Wildman, W.C. J. Org. Chem., 1971, 36, 3202.
3. (a) Grigg, R.; Thianpantangul, S. J. Chem. Soc., Perkin Trans. 1, 1984, 653;
4. (b) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W.J. Tetrahedron Lett., 1990, 31, 559;
5. (c) Grigg, R.; Heaney, F.; Markandu, J.; Surendrakumar, S.; Thornton-Pett, M.; Warnock, W.J. Tetrahedron, 1991, 47, 4007.
6. Norman, M.H.; Heathcock, C.H. J. Org. Chem., 1987, 52, 226.
7. (a) Padwa, A.; Chiacchio, U.; Dean, D.C.; Schoffstall, A.M.; Hassner, A.; Murthy, K.S.K. Tetrahedron Lett., 1988, 29, 4169;
8. (b) Hassner, A.; Maurya, R.; Mesko, E. Tetrahedron Lett., 1988, 29, 5313;
9. (c) Hassner, A.; Maurya, R. Tetrahedron Lett., 1989, 30, 2289;
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11. (e) Hassner, A.; Maurya, R.; Padwa, A.; Bullock, W.H. J. Org. Chem., 1991, 56, 2775;
12. (f) Hassner, A.; Maurya, R.; Padwa, A.; Bullock, W.H. J. Org. Chem., 1991, 56, 2775;
13. (g) Hassner, A.; Maurya, R.; Friedman, O.; Gottlieb, H.E.; Padwa, A.; Austin, D.; J. Org. Chem., 1993, 58, 4539.
14. (a) Arnone, A.; Cavicchioli, M.; Donadelli, A.; Resnati, G. Tetrahedron: Asymmetry, 1994, 5, 1019;
15. (b) Baskaran, S.; Aurich, H.G., Synlett, 1998, 277.
16. Intramolecular nitrone cycloadditions of carbohydrate derived precursors have been described, see (a) Bernet, B.; Vasella, A.; Helv. Chim. Acta, 1979, 62, 1990;
17. (b) Bernet, B.; Vasella, A.; Helv. Chim. Acta, 1979, 62, 2400;
18. (c) Ferrier, R.J.; Furneaux, R.H.; Prasit, P.; Tyler, P.C.; Brown, K.L.; Gainsford, G.J.; Diehl, J.W. ; J. Chem. Soc., Perkin Trans. 1, 1983, 1621.
19. All new compounds have been fully characterised using standard spectroscopic and analytical techniques.
20. 2), 75.4 (C-4), 85.3 (C-6), 86.1 (C-7 & C-8), 127.3 (CH), 127.4 (CH), 127.55 (CH), 127.63 (CH), 127.68 (CH), 127.74 (CH), 128.24 (CH), 128.27 (CH), 128.33 (CH), 138.9 (C), 139.1 (C), 139.3 (C). Selected nOe data: irradiation of H-1 enhances H-5 (9.6%), H-7 (2.8%), H-8 (2.0%) and NH (5.0%); irradiation of H-5 enhances H-1 (9.4%) and H-4 (3.1%).
21. For a discussion and leading reference, see reference 6a.