Oxidation of sterically hindered alkoxysilanes and phenylsilanes under basic conditions

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 6044-6046

  Smitrovich, Jacqueline H ^a   Woerpel, K A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000080248     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960921l     Document Type: Article

References (22)

1. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
2. Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599-7662.
3. Fleming, I.; Henning, R.; Plaut, H. J. Chem. Soc., Chem. Commun. 1984, 29-31.
4. Fleming, I.; Sanderson, P. E. J. Tetrahedron Lett. 1987, 28, 4229-4232.
5. Andrey, O.; Landais, Y.; Planchenault, D. Tetrahedron Lett. 1993, 34, 2927-2930.
6. For example, see: Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671.
7. Bodnar, P. M.; Palmer, W. S.; Shaw, J. T.; Smitrovich, J. H.; Sonnenberg, J. D.; Presley, A. L.; Woerpel, K. A. J. Am. Chem. Soc. 1995, 117, 10575-10576.
8. Clive, D. L. J.; Cantin, M. J. Chem. Soc., Chem. Commun. 1995, 319-320.
9. Furthermore, each diastereomer of 1 was oxidized to a stereochemically unique diol, and reference diols were prepared for comparison (ref 7).
10. El-Durini, N. M. K.; Jackson, R. A. J. Organomet. Chem. 1982, 232, 117-121.
11. Semenov, V. V.; Ladilina, E. Y.; Chesnokova, T. A.; Cherepennikova, N. F. Zh. Obshch. Khim. 1991, 61, 1184-1195.
12. 13C NMR spectroscopy and by GC.
13. (a) Beauchamp, T. J.; Powers, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 1995, 117, 12873-12874.
14. (b) Beauchamp, T. J.; Rychnovsky, S. D., University of California, Irvine, personal communication, 1996.
15. For an example of the use of hindered alkoxysilanes to control the stereochemistry in a cyclization reaction, see: Lipshutz, B. H.; Tirado, R. J. Org. Chem. 1994, 59, 8307-8311.
16. Magar, S. S.; Fuchs, P. L. Tetrahedron Lett. 1991, 32, 7513-7516.
17. Murakami, M.; Suginome, M.; Fujimoto, K.; Nakamura, H.; Andersson, P. G.; Ito, Y. J. Am. Chem. Soc. 1993, 115, 6487-6498.
18. Taber, D. F.; Yet, L.; Bhamidipati, R. S. Tetrahedron Lett. 1995, 36, 351-354.
19. Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett. 1995, 36, 2987-2990.
20. Knolker, H. J.; Wanzl, G. Synlett 1995, 378-382.
21. Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501-504.
22. Molander and Nichols have employed the oxidation protocol reported here as their final step of an expeditious synthesis of epilupinine in the accompanying paper: Molander, G. A.; Nichols, P. J. J. Org. Chem. 1996, 61, 6040-6043.