Benzosilacyclohexadienones: Synthesis and reactivity

Tetrahedron Letters

Volumn 40, Issue 45, 1999, Pages 7901-7906

  Kende, Andrew S ^a   Mineur, Catherine M ^a   Lachicotte, Rene J ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

1,4 addition; Allylic oxidation; Benzosilacyclohexenes; Cyanocuprate addition; Cyclic silyl , unsaturated ketones; Diels Alder reaction; Mukaiyama re action; Zinc bromide catalyst

Indexed keywords

CYCLOHEXENE DERIVATIVE; KETONE DERIVATIVE; ZINC BROMIDE;

ARTICLE; CATALYST; CHEMICAL REACTION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

BETULACEAE;

EID: 0033527774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01494-X     Document Type: Article

References (36)

1. (a) Barton, T. J.; Banasiak, D. S. J. Organomet. Chem. 1978, 157, 255.
2. (b) Harada, T.; Imanaka, S.; Ohyama, Y.; Matsuda, Y.; Oku, A. Tetrahedron Lett. 1992, 33, 5807.
3. (c) Garland, R. B.; Palmer, J. R.; Schulz, J. A.; Sollman, P. B.; Pappo, R. Tetrahedron Lett. 1970, 3669.
4. (d) Bovicelli, P.; Mincione, E.; Parsons, P. J. Synth. Commun. 1988, 18, 1231.
5. (e) Pillot, J.-P.; Dunogues, J.; Calas, R. Bull. Soc. Chim. Fr. 1975, 2143.
6. (f) Felix, R. A.; Weber, W. P. J. Org. Chem. 1972, 37, 2323.
7. (a) Sakurai, H.; Imai, T. Chemistry Lett. 1975, 891.
8. (b) Takeyama, Y.; Nozaki, K.; Matsumoto, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1461.
9. (a) De Lucchi, O.; Modena, G. Tetrahedron 1984, 40, 2585.
10. (b) Bhattacharya, S. N.; Josiah, B. M.; Walton, D. R. M. Organometallics in Chemical Synthesis 1970/1971, 1, 145.
11. (c) Waykole, L.; Paquette, L. A. Organic Syntheses 1988, 67, 149.
12. (d) Chen, Z.; Trudell, M. L. Synth. Commun. 1994, 24, 3149.
13. 2 (Siemens, SHELXTL, version 5.04). The non-H atoms for all the structures were refined with anisotropic thermal parameters. The H atoms were located and their positions and isotropic thermal parameters were refined for compounds 2 and 10, and for compound 4c the H atoms were included in idealized positions.
14. 3. (equations presented)
15. (a) Hartman, G. D.; Phillips, B. T.; Halcenko, W. J. Org. Chem. 1985, 50, 2423.
16. (b) Harmata, M.; Barnes, C. L. Tetrahedron Lett. 1990, 31, 1825.
17. (c) Hanessian, S.; Vanasse, B. Can. J. Chem. 1987, 195.
18. (a) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021.
19. (b) Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173.
20. (c) Bestmann, H. J.; Rippel, H. C.; Dostalek, R. Tetrahedron Lett. 1989, 30, 5261.
21. (a) Shinobuko, H.; Miki, H.; Yokoo, T.; Oshima, K.; Utimoto, K. Tetrahedron 1995, 51, 11681.
22. (b) Maercker, A.; Bodenstedt, H.; Brandsma, L. Angew. Chem., Int. Ed. Engl. 1992, 31, 1339.
23. +.), 159, 143, 131. HR-MS (EI): found: 174.0859.
24. Feng, S.; Klosin, J.; Kruper, W. J.; McAdon, M. H.; Neithamer, D. R.; Nickias, P.; Patton, J. T.; Wilson, D. R.; Abboud, K. A.; Stern, C. L. Organometallics 1999, 18, 1159.
25. +.), 235. HR-MS (EI): found: 312.0974.
26. Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404.
27. -1): 3274, 3050, 2959, 2898, 1948, 1845, 1677, 1643, 1578, 1433. HR-MS (EI): found: 188.0653.
28. 3.
29. (a) Fleming, I.; Patel, S. K.; Urch, C. J. J. Chem. Soc., Perkin Trans. 1 1989, 115.
30. (b) Fleming, I.; Perry, D. A. Tetrahedron 1981, 37, 4027.
31. (c) Fleming, I.; Patel, S. K. Tetrahedron Lett. 1981, 22, 2321.
32. 3. (equations presented)
33. Brook, A. G.; Duff, J. M. Can. J. Chem. 1973, 2024.
34. Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. J. Org. Chem. 1984, 3938.
35. (a) Rathke, M. W.; Sullivan, D. F. Synth. Commun. 1973, 3, 67.
36. (b) Kita, Y.; Segawa, J.; Haruta, J.; Yasuda, H.; Tamura, Y. J. Chem. Soc., Perkin Trans. 1 1982, 1099.