The ultra high pressure conjugate addition of indoles to electron- deficient olefins

Canadian Journal of Chemistry

Volumn 76, Issue 9, 1998, Pages 1256-1265

  Harrington, Paul ^a   Kerr, Michael A ^a  

^a ACADIA UNIVERSITY   (Canada)

Author keywords

Hapalindole; High pressure; Indole; Lewis acid; Michael addition; Ytterbium triflate

Indexed keywords

3 METHYLCYCLOHEX 2 EN 1 ONE; ALKENE; INDOLE ALKALOID; INDOLE DERIVATIVE; KETONE DERIVATIVE; MALONIC ACID DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG; YTTERBIUM;

ALKYLATION; ARTICLE; CONJUGATE; PRESSURE; STEREOSPECIFICITY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0032411573     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v98-158     Document Type: Article

References (31)

1. (a) R.E. Moore, C. Cheuk, X.-Q. Yang, G.M.L. Patterson, R. Bonjouklian, T.A. Smitka, J. Mynderse, R.S. Foster, N.D. Jones, J.K. Swartzendruber, and J.B. Deeter. J. Org. Chem. 52, 1036 (1987);
2. (b) R.E. Moore, C. Cheuk, and G.M.L. Patterson. J. Am. Chem. Soc. 106, 6456 (1984).
3. R. Bonjouklian, R.E. Moore, and G.M.L. Patterson. J. Org. Chem. 53, 5866 (1988).
4. (a) M. Sakagami, H. Muratake, and M. Natsume. Chem. Pharm. Bull. 42, 1393 (1994);
5. (b) T. Fukuyama and X. Chen. J. Am. Chem. Soc. 116, 3125 (1994);
6. (c) V. Vaillancouirt and K.F. Albizati. J. Am. Chem. Soc. 115, 3499 (1993);
7. (d) H. Muratake, H. Kumagami, and M. Natsume. Tetrahedron, 46, 6351 (1990);
8. (e) H. Muratake and M. Natsume. Tetrahedron, 46, 6331 (1990);
9. (f) H. Muratake and M. Natsume. Tetrahedron Lett. 1815 (1989).
10. R.J. Sunnberg. The chemistry of indoles. Academic Press, New York. 1970.
11. (a) J. Szmuszkovic. J. Am. Chem. Soc. 79, 2819 (1957);
12. (b) W.E. Noland, G,M. Christensen, G.L. Sauer, and G.G.S. Dutton. J. Am. Chem. Soc. 77, 456 (1955);
13. (c) R.L. Garnick, S.B. Levery, and P.W. Le Quesne. J. Org. Chem. 43, 1226 (1978), and refs. cited therein;
14. (d) Z. Iqbal, A.H. Jackson, and K.R.N. Rao. Tetrahedron Lett. 2577 (1988);
15. (e) G. Dujardin and J.-M. Poirer. Bull. Soc. Chim. Fr. 131, 900 (1994).
16. H. Kotsuki, M. Teraguchi, N. Shimomoto, and M. Ochi. Tetrahedron Lett. 3727 (1996).
17. P.E. Harrington and M.A. Kerr. Synlett, 1047 (1996).
18. (a) R.W. Marshman. Aldrichimica Acta, 28, 77 (1995);
19. (b) S. Kobayashi. Synlett, 689 (1994).
20. G. Jenner. Tetrahedron Lett. 233 (1995).
21. (a) S. Kobayashi, M. Moriwaki, and I. Hachiya. Synlett, 1153 (1995);
22. (b) S. Kobayashi, S. Mitamura, and A. Kawada. Chem. Commun. 1157 (1993).
23. (a) K. Freter. J. Org. Chem. 37, 2010 (1972);
24. (b) J. Org. Chem. 40, 2525 (1975).
25. D. Chen, L. Yu, and P.G. Wang. Tetrahedron Lett. 4467 (1996).
26. (a) N.S. Isaacs. High pressure techniques in chemistry and physics: a practical approach. Edited by W.B. Holzapfel and N.S. Isaacs. Oxford University Press, New York. 1997. p. 307;
27. (b) F.-G. Klarner, M.K. Diedrich, and A.E. Wigger. Chemistry under extreme or non-classical conditions. Edited by R. van Eldik and C.D. Hubbard. John Wiley and Sons, New York. 1997. p. 53.
28. (a) R.A. Bounce, M.F. Schlecht, W.G. Dauben, and C.H. Heathcock. Tetrahedron Lett. 4943 (1983);
29. (b) W.G. Dauben and J.M. Gerdes. Tetrahedron Lett. 3841 (1983);
30. (c) W.G. Dauben and R.A. Bounce. J. Org. Chem. 48, 4642 (1983);
31. (d) W.G. Dauben and H.O. Krabbenhoft. J. Org. Chem. 42, 282 (1977).