Mechanistic Study of the Jacobsen Asymmetric Epoxidation of Indene

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 2222-2229

  Hughes, David L ^a   Smith, George B ^a   Liu, Ji ^a   Dezeny, George C ^a   Senanayake, Chris H ^a   Larsen, Robert D ^a   Verhoeven, Thomas R ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000496736     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961735i     Document Type: Article

References (21)

1. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
2. (a) Hart, H.; Lavrik, P. B. J. Org. Chem. 1974, 39, 1793.
3. (b) Sheldon, R. A. Recl. Trav. Chim. Pays-Bas 1973, 92, 253.
4. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
5. Groves, J. T.; Meyers, R. S. J. Am. Chem. Soc. 1983, 105, 5791.
6. Srinivasan, K.; Michaud, P.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309-2320. Srinivasan, K.; Perrier, S.; Kochi, J. K. J. Mol. Catal. 1986, 36, 297-317.
7. Srinivasan, K.; Michaud, P.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309-2320. Srinivasan, K.; Perrier, S.; Kochi, J. K. J. Mol. Catal. 1986, 36, 297-317.
8. Yoon, H.; Burrows, C. J. J. Am. Chem. Soc. 1988, 110, 4087.
9. Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801.
10. Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; pp 159-202.
11. (a) Collman, J. P.; Brauman, J. I.; Meunier, B.; Raybuck, S. A.; Kodadek, T. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 3245-3248.
12. (b) Collman, J. P.; Brauman, J. I.; Meunier, B.; Hayashi, T.; Kodadek, T.; Raybuck, S. A. J. Am. Chem. Soc. 1985, 107, 2000-2005.
13. (c) Collman, J. P.; Brauman, J. I.; Hampton, P. D.; Tanaka, H.; Bohle, D. S.; Hembre, R. T. J. Am. Chem. Soc. 1990, 112, 7980-7984.
14. Norrby, P.-O.; Linde, C.; Akermark, B. J. Am. Chem. Soc. 1995, 117, 11035-11036.
15. Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515-530.
16. Finney, N. S.; Pospisil, P. J.; Chang, S.; Palucki, M.; Hansen, K. B.; Jacobsen, E. N. Private communication.
17. Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
18. Senanayake, C. H.; Smith, G. B.; Ryan, K. M.; Fredenburgh, L. E.; Liu, J.; Roberts, F. E.; Hughes, D. L.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 3271-3274.
19. 3NO is dissolved initially, and interpretation is more complex since the level changes throughout the reaction.
20. Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 9333-9334.
21. 14 indicated that the pyridine cannot be oxidized to the N-oxide under the reaction conditions, so it is unlikely that a catalytic cycle exists involving the pyridine and its N-oxide.