Palladium-mediated carbosubstitutions in spiranes

Tetrahedron

Volumn 55, Issue 28, 1999, Pages 8525-8538

  Falck Pedersen, Mette Lene ^a   Rømming, Christian ^a   Undheim, Kjell ^a  

^a UNIVERSITY OF OSLO   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SPIRANE; SPIRO[4,4]NONANE 1,6 DIONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; ENANTIOMER; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033538626     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00470-6     Document Type: Article

References (51)

1. 1. (a) Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T., The Total synthesis of Sesquiterpines, ed. ApSimon, J., Wiley, New York, 1983, vol. 5, pp. 264-313;
2. (b) Vandewalle, M.; De Clercq, P. Tetrahedron 1985, 41, 1767-1831;
3. (c) Hwu, J. R.; Wetzel, J. M. J. Org. Chem. 1992, 57, 922-928;
4. (d) Kido, F.; Abiko, T.; Kato, M. J. Chem. Soc., Perkin Trans. 1 1992, 229-233;
5. (e) Mori, M.; Ishono, N.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1993, 58, 2972-2976.
6. 2 (a) Gerlach, H.; Müller, W. Helv. Chim. Acta 1972, 55, 2277-2286;
7. (b) Gerlach, H. Helv. Chim. Acta 1968, 51, 1587-1593;
8. (c) Cram, D. J.; Van Duuren, B. L. J. Am. Chem. Soc. 1955, 77, 3576-3579;
9. (d) Hardegger, E.; Maeder, E.; Semarne, H. M.; Cram, D. J. J. Am. Chem. Soc. 1959, 81, 2729-2737;
10. (e) Harada, N.; Ai, T.; Uda, H. J. Chem. Soc., Chem. Commun. 1982, 232-233;
11. (f) Sumiyoshi, M.; Kuritani, H.; Shingu, K. J. C. S., Chem. Commun. 1977, 812-814.
12. 3. Srivastava, N.; Mital, A.; Kumar, A. J. Chem. Soc., Chem. Commun. 1992, 493-494.
13. 4. Jiang, Y.; Xue, S.; Li, Z.; Deng, J.; Mi, A.; Chan, A. C. Tetrahedron: Asymmetry 1998, 9, 3185-3189.
14. 5. (a) Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y., Liu, F. Chem. Rev. 1996, 96, 365-393;
15. (b) Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1996, 37, 695-698 and references therein;
16. (c) Ripa, L.; Hallberg, A. J. Org. Chem. 1997, 62, 595-602.
17. 6. (a) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421-9438;
18. (b) Trost, B. M; Lautens, M; Chan, C.; Jebaratnam, D. J.; Mueller, T. J. Am. Chem. Soc. 1991, 113, 636-644;
19. (c) Overman, L. E.; Abelman, M. M.; Kucera, D. J.; Tran, V. D.; Ricca, D. J. Pure Appl. Chem. 1992, 64, 1813-1819;
20. (d) Wu, G.-z.; Lamaty, F.; Negishi, E-i. J. Org. Chem. 1989, 54, 2507-2508.
21. 7. (a) Back, T. G.; Gladstone, P. L.; Parvez, M. J. Org. Chem. 1996, 61, 3806-3814;
22. (b) Clive, D. L. J.; Bengstra, R. J. J. Org. Chem. 1990, 55, 1786-1792;
23. (c) Cossy, J.; Gille, B.; Bellosta, V. J. Org. Chem. 1998, 63, 3141-3146.
24. 8. (a) Liu, P.-Y.; Wu, Y.-J.; Burnell, D. J. Can. J. Chem. 1997, 75, 656-664;
25. (b) Wu, Y.-J.; Zhu, Y.-Y.; Burnell, D. J. J. Org. Chem. 1994, 59, 104-110;
26. (c) Zhu, Y.-Y.; Burnell, D. J. Tetrahedron: Asymmetry 1996, 7, 3295-3304.
27. 9. Patra, D.; Ghosh, S. J. Chem. Soc. Perkin Trans 1 1995, 2635-2641.
28. 10. Kong, K.-C; Cheng, C.-H. Organometallics, 1992, 11, 1972-1975.
29. 11. Sattelkau, T; Hollmann, C; Eilbracht, P. Synlett 1996, 1221-1223.
30. 12. Wender, P. A.; White, A. W. J. Am. Chem. Soc. 1988, 110, 2218-2223.
31. 13. Molander, G. A.; Alonso-Alija, C. Tetrahedron 1997, 55, 8067-8084.
32. 14. (a) Yamada, S.; Karasawa, S.; Takahashi, Y.; Aso, M.; Suemune, H. Tetrahedron 1998, 54, 15555-15566;
33. (b) Wu, Y.; Ahlberg, P. Acta Chem. Scand. 1995, 49, 364-374;
34. (c) Schmidt, W.; Vögtle, F.; Poetsch, E. Liebigs Ann 1995, 1319-1326;
35. (d) Melmer, M.; Neudeck, H.; Schlögl, K.; Werner, A. Monatshefte Chem. 1995, 126, 933-943;
36. (e) Neudeck, H. K. Monatshefte Chem. 1995, 126, 1125-1144;
37. (f) Neudeck, H. K. Monatshefte Chem. 1996, 127, 417-434.
38. 15. (a) Galvez, J. M. G.; Angers, P.; Canonne, P. Tetrahedron Lett. 1994, 35, 2849-2852;
39. (b) Maezaki, N.; Fukuyama, H.; Yagi, S.; Tanaka, T.; Iwata, C. J. Chem. Soc., Chem. Commun. 1994, 1835-1836.
40. 16. Aburel, P. S.; Undheim, K. Tetrahedron Lett. 1998, 39, 3813-3814.
41. 17. Möller, B.; Undheim, K. Tetrahedron 1998, 54, 5789-5804.
42. 18. (a) Hammer, K.; Undheim, K. Tetrahedron, 1997, 53, 2309-2322;
43. (b) Krikstolaityté, S.; Hammer, K.; Undheim, K. Tetrahedron Lett. 1998, 39, 7595-7598;
44. (c) Hammer, K.; Undheim, K. Tetrahedron 1997, 53, 10603-10614.
45. 19. (a) Gerlach, H.; Müller, W. Angew. Chem., Int. Ed. Engl. Ed. 1972, 11, 1030-1031;
46. (b) Nieman, J. A.; Parvez, M.; Keay, B. A. Tetrahedron: Asymmetry 1993, 4, 1973-1976.
47. 20. Nakayama, J. and Fujimori, T. J. Chem. Soc., Chem. Commun. 1991, 1614-1615.
48. 21. Nieman, J. A.; Keay, B. A. Tetrahedron: Asymmetry 1995, 6, 1575-1583.
49. 22. SMART and SAINT Area-detector Control and Integration Software, Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
50. 23. Sheldrick, G. M. Private communication, 1996.
51. 24. Sheldrick, G. M. SHELXTL, Version 5. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.