The bis(homoallylic) stabilisation of an acyliminium ion and reactions with nucleophiles

Tetrahedron Letters

Volumn 39, Issue 20, 1998, Pages 3341-3344

  Heaney, Harry ^a   Taha, Mutasem O ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLIMINIUM DERIVATIVE; BIS(HOMOALLYL) DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; CYCLIZATION; PROTEIN STABILITY; REACTION ANALYSIS;

EID: 0032516311     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00486-9     Document Type: Article

References (33)

1. 1. (a) Speckamp, W.N.; Hiemstra, H. Tetrahedron, 1985, 41, 4367-4416;
2. (b) Hiemstra, H.; Speckamp, W.N. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I. Eds.; Pergamon, Oxford, 1991, vol.2, pp 1047-1082.
3. 2. (a) Heaney, H.; Shuhaibar, K.F. Tetrahedron Lett., 1994, 35, 2751-2752;
4. (b) Heaney, H.; Shuhaibar, K.F. Synlett, 1995, 47-48;
5. (c) El Gihani, M.T.; Heaney, H.; Shuhaibar, K.F. Synlett, 1996, 871-872.
6. 3. (a) Schoemaker, H.E.; Speckamp, W.N. Tetrahedron, 1978, 34, 163-172;
7. (b) Nossin, P.M.M.; Speckamp, W.N. Tetrahedron Lett., 1980, 21, 1991-1994;
8. (c) Hart, D.J.; Hong, W.-P. J. Org. Chem., 1985, 50, 3670-3672;
9. (d) Hart, D.J.; Yang, T.-K. J. Org. Chem., 1985, 50, 235-242;
10. (e) Ent, H.; de Koning, H.; Speckamp, W.N. J. Org. Chem., 1986, 51, 1687-1691.
11. 4. (a) Lochead, A.W.; Proctor, G.R.; Caton, M.P.L. J. Chem. Soc., Perkin Trans. 1, 1984, 2477-2489;
12. (b) Chamberlin, A.R.; Nguyen, D.H.; Chung, J.Y.L. J. Org. Chem., 1984, 49, 1682-1688;
13. (c) Hiemstra, H.; Sno, M.H.A.M.; Vijn, R.J.; Speckamp, W.N. J. Org. Chem., 1985, 50, 4014-4020;
14. (d) Keck, G.E.; Cressman, E.N.K.; Enholm, E.J. J. Org. Chem., 1989, 54, 4345-4349.
15. 5. (a) Flann, C.; Overman, L.E. J. Am. Chem. Soc., 1987, 109, 6115-6118;
16. (b) Heitz, M.-P.; Overman, L.E. J. Org. Chem., 1989, 54, 2591-2596.
17. 6. (a) Collado, M.I.; Manteca, I.; Sotomayor, N.; Villa, M.J.; Lete, E. J. Org. Chem., 1997, 62, 2080-2092;
18. (b) Pigeon, P.; Decroix, B. Tetrahedron Lett., 1997, 38, 2985-2988;
19. (c) Lee, Y.S.; Lee, J.Y.; Park, H. Synthetic Commun., 1997, 27, 2799-2812;
20. (d) Fisher, M.J.; Gunn, B.P.; Um, S.; Jakubowski, J.A. Tetrahedron Lett., 1997, 38, 5747-5750;
21. (e) Luker, T.; Hiemstra, H., Speckamp, W.N. J. Org. Chem., 1997, 62, 8131-8140;
22. (f) Comins, D.L.; Thakker, P.M.; Baevsky, M.F.; Badawi, M.M. Tetrahedron, 1997, 53, 16327-16340.
23. 7. Heaney, H.; Taha, M.O. Synlett, 1996, 820-822.
24. 8. (a) Würthwein, E.-U.; Kupfer, R.; Kaliba, C. Angew. Chem. Suppl., 1983, 264-270;
25. (b) see also in ref. 1 (a) ref 4;
26. (c) Yamamoto, Y.; Nakada, T.; Nemoto, H. J. Am. Chem. Soc., 1992, 114, 121-125.
27. 13C HETCOR experiments.
28. 10. (a) Wanner, K. Th.; Höfner, G. Arch. Pharm. (Weinheim), 1990, 323, 977-986;
29. (b) El Gihani, M.; Heaney, H. Synlett, 1993, 433-434;
30. (c) for a review on the use of BSA see: El Gihani, M.T.; Heaney, H. Synthesis, 1998, in press.
31. 13C HETCOR experiments.
32. 2), 127.0 (CH), 127.2 (CH), 127.3 (C), 128.1 (CH), 128.4 (CH), 129.0 (2×CH), 129.3 (2×CH), 130.5 (CH), 132.7 (CH), 133.3 (CH), 136.2 (CH), 138.1 (C), 142.2 (C), and 163.3 (C=O) ppm.
33. 1H NOESY experiments.